165 Fun Facts About Kentucky Derby

Which horse won the very first Kentucky Derby?

Aristides was meant to be the pacemaking 'rabbit' for his stablemate Chesapeake, but simply never came back to the field.

Over what distance has the Kentucky Derby been run since 1896?

1 and 1/4 miles, or ten furlongs, takes the field about two minutes to cover, which is why the Derby is billed as 'the most exciting two minutes in sports'.

Which horse was the first to run the Kentucky Derby in under two minutes?

Secretariat won the 1973 Derby in 1:59 2/5, running each quarter-mile faster than the one before, so he was still accelerating as he reached the finish.

What traditional beverage is most associated with the Kentucky Derby?

Mint Julep, a mix of bourbon, sugar syrup and mint over crushed ice, became the Derby's official drink in the 1930s, when Churchill Downs began serving it in souvenir cups that racegoers could keep.

Which song is played as the horses parade before the grandstand ahead of the Kentucky Derby?

My Old Kentucky Home, by Stephen Foster, is played by the University of Louisville marching band as the horses parade; at the crowdless 2020 Derby a lone bugler played it instead.

Which 1932 winner was the first to wear the modern Garland of Roses?

Louisville florist Grace Walker designed the garland at the request of Churchill Downs official Samuel Culbertson.

Queen Elizabeth II's 2007 Derby trip came on a visit marking which settlement's 400th anniversary?

Jamestown had welcomed her before: she came for its 350th anniversary in 1957, and fifty years on she returned, then went on to Churchill Downs for her first Derby.

Which two jockeys each won the Kentucky Derby five times?

Eddie Arcaro and Bill Hartack each won five; Hartack's first, on Iron Liege in 1957, came by a nose after the rival jockey stood up in his stirrups too soon, mistaking a marker pole for the finish line.

Who founded Churchill Downs and organized the first Kentucky Derby?

Meriwether Lewis Clark Jr. opened the track in 1875 on land that belonged to his mother's family, the Churchills, and within a decade it was being called by their name.

Which horse was the first Triple Crown winner in history?

Sir Barton had never won a race before the 1919 Derby, then swept the series in about a month.

Which feature atop the Churchill Downs grandstand has become the Derby's symbol?

The Twin Spires were not in the first plans: Joseph Baldez, the 24-year-old draftsman drawing up the 1895 grandstand, added them because he felt the building needed something striking.

Which trainer matched Ben Jones's six Kentucky Derby wins when Authentic won in 2020?

Bob Baffert drew level with Ben Jones when Authentic won in 2020; a seventh winner, Medina Spirit in 2021, was later disqualified over a failed drug test, leaving him on six.

In which city is Churchill Downs located?

Churchill Downs is in Louisville, Kentucky, about three miles south of downtown, and has hosted the Derby every year since its first running.

Which filly became the first of her sex to win the Kentucky Derby, in 1915?

Regret's win brought the race a wave of national newspaper coverage and is credited with turning a regional event into an American institution.

Which gray colt, an early television star, suffered the only defeat of his career in the 1953 Kentucky Derby?

Native Dancer lost by a head to 25-1 shot Dark Star, then won the Preakness and Belmont and retired with 21 wins from 22 starts.

Which 91-1 longshot won the 1913 Kentucky Derby?

Donerail won at 91-1 and paid $184.90 for a $2 bet, and it was no slow fluke: his 2:04 4/5 was the fastest Derby run up to that time.

Which horse won the 2015 Triple Crown, the first sweep in 37 years?

American Pharoah's misspelt name came from a fan's winning entry in his owner's naming contest, which was sent on to the Jockey Club before anyone caught the error.

Since 2013, horses have earned a place in the Kentucky Derby starting gate by collecting what in designated prep races?

Points replaced a ranking by graded-stakes earnings, which had counted money won in sprints, turf races and two-year-old races as much as the traditional Derby preps.

The Kentucky Derby's founder modelled it on the signature race of which English racecourse?

Epsom's Derby had been run every year since 1780 when the Kentucky race's founder came to watch in 1872; he went home and set up a jockey club to stage an American version.

Which color are racegoers encouraged to wear at Churchill Downs on Kentucky Oaks day?

Pink marks the Oaks-day campaign for breast and ovarian cancer awareness, when survivors of both diseases walk the track in a parade of their own.

Which colt ran second in the 1973 Kentucky Derby in a time quick enough to win almost any other Derby?

Sham finished 2½ lengths behind the record-setting winner despite smashing his mouth on the starting gate at the break, and many observers reckon he too finished inside two minutes.

What color are the roses in the Kentucky Derby winner's garland?

Red roses became the Derby's official flower in 1904; the first garland on record, presented to the 1896 winner, was not red at all.

Which runner-up was declared the winner of the 2021 Kentucky Derby after Medina Spirit was disqualified?

Mandaloun finished half a length behind on the day and was promoted only in February 2022, more than nine months later, after the first horse home failed a drug test.

Roughly how many of its signature cocktails does Churchill Downs serve over the two days of Derby weekend?

120,000 or so are poured across the two days, and nearly all of them go out in collectible souvenir glasses that many racegoers take home.

Which open-faced sandwich, a Kentucky Derby party favourite, was created at a Louisville hotel in the 1920s?

Hot Brown was a chef's answer to dinner-dance guests who wanted something grander than ham and eggs in the small hours: turkey and bacon on toast under a cheese sauce.

Which horse won the 2022 Kentucky Derby as a massive 80-1 longshot?

Rich Strike stunned the racing world by winning the 2022 Kentucky Derby at 80-1 odds, paying $163.60 on a $2 win bet. He was only added to the field after a late scratch.

Every Kentucky Derby runner officially turns three on which holiday?

New Year's Day is the official birthday of every Thoroughbred in the Northern Hemisphere, whatever day it was foaled, so a colt born in late spring runs the Derby before he has really turned three.

Which trainer won four Kentucky Derbies including Winning Colors in 1988 and Thunder Gulch in 1995?

D. Wayne Lukas won with Winning Colors, Thunder Gulch, Grindstone and Charismatic; in 1995 he took all three Triple Crown races with two different horses, something no trainer had done before.

Which 1968 winner was the first Derby winner ever to be disqualified, after a post-race drug test?

Dancer's Image crossed the line first in 1968, but a urine test found traces of the painkiller phenylbutazone; after a long legal fight the win went to Forward Pass.

Which 1941 Triple Crown winner was known for come-from-behind runs and a distinctive long tail?

Whirlaway, nicknamed 'Mr. Longtail', kept veering toward the outside rail, so trainer Ben Jones fitted a blinker that covered his right eye, and the colt ran straight to win the Derby in record time.

Mine That Bird's trainer drove the 2009 Derby winner to Kentucky by pickup and trailer from which state?

New Mexico was home base for trainer Chip Woolley, who made the 21-hour drive himself while on crutches after a motorcycle accident; Mine That Bird then won at 50-1.

Which 2001 winner became only the second horse to win the Kentucky Derby in under two minutes?

Monarchos won in 1:59.97, beating the favourite Point Given, who ran unplaced but went on to take the Preakness and Belmont and be voted Horse of the Year.

Roughly how large is the total purse the Kentucky Derby has offered since its 2024 increase?

$5 million, of which $3.1 million goes to the winner; the purse first reached $1 million only in 1996, so it has grown fivefold in under thirty years.

Which supermarket chain's florists have made the Kentucky Derby winner's garland since 1987?

Kroger's florists build it in one of the chain's local stores on Derby Eve, where the public can watch more than 400 roses being sewn onto the satin backing by hand.

Which horse won the 1948 Triple Crown, the last sweep for 25 years?

Citation swept the 1948 Triple Crown so completely that no rival would face him in that autumn's Pimlico Special, which he won in a walkover; the next sweep did not come until 1973.

Which horse won the 1977 Triple Crown as the first ever undefeated Triple Crown winner?

Bought for just $17,500 as a yearling, Seattle Slew was nine-for-nine when he completed the sweep at the Belmont.

Which Kentucky farm, famed for its devil's-red silks, owned a record eight Derby winners between 1941 and 1968?

Calumet Farm's eighth and last, Forward Pass in 1968, crossed the line second and was handed the race only when the first horse home failed a drug test.

What fashion accessory is most famously associated with Kentucky Derby spectators?

Hats are the showpiece of Derby dress, grandest in the box seats of 'Millionaire's Row', while the infield crowd across the track treats the day as one long party.

Which US network has televised the Kentucky Derby every year since 2001?

NBC took over from ABC, which had shown the race since 1975; the first national telecast, back in 1952, came from a CBS station.

Which jockey rode the first-ever Triple Crown winner in the 1919 Kentucky Derby?

Johnny Loftus rode the colt, a maiden before that Derby, and completed the first Triple Crown sweep on him in the Belmont Stakes on June 11, 1919.

Which sportswriter coined the term 'Run for the Roses' for the Kentucky Derby?

Corum coined the phrase in 1925 and later spent nine years as president of Churchill Downs.

Which of these was a Kentucky Derby first in 2019?

A winner disqualified for interference was new to the Derby: stewards took down Maximum Security for swerving into rivals on the far turn and gave the race to 65-1 shot Country House.

On which day of the week is the Kentucky Derby traditionally run?

Saturday has long been Derby day, yet the very first running in 1875 took place on a Monday.

Which trainer became the first woman to saddle a Kentucky Derby winner when Golden Tempo won in 2026?

Cherie DeVaux's colt, a 23-1 shot, came from well back to catch the co-favourite at the line; no woman had trained the winner in the race's first 151 runnings.

Before the 2020 pandemic, the only Kentucky Derby ever postponed was delayed by which event?

World War II led the government to suspend all racing from January 1945; the order was lifted days after victory in Europe, and the Derby went ahead on June 9, five weeks late.

Which 18-year-old jockey rode Affirmed to the 1978 Triple Crown?

Steve Cauthen later moved abroad, where he was champion jockey three times and twice won the original Derby, the race Kentucky's was modelled on.

Which French race did Meriwether Lewis Clark Jr. also visit for inspiration in 1872?

Clark took in the Grand Prix de Paris, run at Longchamp since 1863 and organised by the French Jockey Club, on the same 1872 trip to Europe.

Which Louisville-based company was the Kentucky Derby's presenting sponsor from 2006 to 2017?

Yum! Brands, the parent of KFC, put its name after the race's in 2006, and for twelve runnings the title read 'the Kentucky Derby presented by Yum! Brands'.

Who rode Secretariat to victory in the 1973 Kentucky Derby?

Ron Turcotte rode Secretariat in all three 1973 Triple Crown races, including the 31-length Belmont; the Canadian jockey was paralysed in a 1978 racing fall.

Which Kentucky Derby winner skipped the Preakness and Belmont to chase a $2 million bonus in New Jersey?

Spend a Buck followed his Derby win with the Jersey Derby three weeks later, a $2.6 million payday that was then the richest in American racing; the Triple Crown tracks answered with a bonus of their own.

Derby-winning jockey Willie Simms is credited with taking America's short-stirrup riding style to which country in 1895?

England first saw the crouching style when Simms rode there, becoming the first American jockey to win on an American horse; later riders such as Tod Sloan made it the norm.

Which colonel joined the 1902 takeover of Churchill Downs and built the Derby into America's leading race?

Matt Winn saw the first Derby as a boy in 1875 and never missed one in his lifetime; the track's 1949 souvenir glass carried his portrait and the line 'He Has Seen Them All'.

Roughly how many people packed Churchill Downs for the Kentucky Derby's record crowd in 2015?

170,000, or 170,513 officially, beat the record of 165,307 set three years earlier; many of them were in the infield, where little of the race can actually be seen.

Which champion skipped the 1920 Kentucky Derby and made his three-year-old debut in the Preakness instead?

Man o' War's owner is said to have thought the race came too early in the year for a young horse; the colt won the Preakness, took the Belmont by 20 lengths and lost only once in his career.

Which 1984 Derby and Belmont winner collapsed and died just eight days after his Belmont victory?

Swale, a son of the 1977 Triple Crown winner, collapsed on the way back to his stall on June 17, 1984; his two classic wins still made his sire that year's leading stallion.

Which rival finished second to Affirmed in all three 1978 Triple Crown races?

Alydar got closer each time: beaten a length and a half in the Derby, a neck in the Preakness and a head in the Belmont, where the pair ran side by side down the stretch to the finish.

Citation was the first horse to reach what earnings milestone?

US$1 million was the target owner Warren Wright set before his death in 1950, so Citation raced on at six, passed the mark in the 1951 Hollywood Gold Cup and was retired at once.

America's first Triple Crown winner, in 1919, carried the silks of a railway heir from which country?

Canada's Commander Jack Ross paid $10,000 for the colt in 1918 and sent him to trainer Guy Bedwell; he was still without a win when he lined up for the Derby.

The 2015 Triple Crown winner completed racing's first 'Grand Slam' by also winning which race?

The Breeders' Cup Classic was his farewell: two months after his only defeat of the year, in the Travers, he led all the way to win by 6½ lengths in track-record time.

Which Hall of Fame jockey won his first Kentucky Derby aboard Mage in 2023?

Javier Castellano followed his first Derby with his first Belmont five weeks later, on a different horse, Arcangelo.

Funny Cide, raced by the Sackatoga Stable partnership, was the first Derby winner bred in which state?

New York had never produced a Derby winner until 2003; his owners' stable name, Sackatoga, blends two towns in the state, Sackets Harbor and Saratoga Springs.

Which Triple Crown winner lost the 1938 'Match Race of the Century' to Seabiscuit?

War Admiral was the heavy favourite and expected to lead from the start, but Seabiscuit beat him to the front, was briefly headed, and drew away to win by four lengths in track-record time.

Which Triple Crown winner took the 1943 Belmont Stakes by a then-record 25 lengths?

Count Fleet hurt an ankle during the 1943 Belmont yet still won by 25 lengths; more leg trouble followed and he never raced again.

Which Texas-bred Triple Crown winner was nicknamed the 'Club-footed Comet'?

Assault, bred at Texas's King Ranch, stepped on something sharp as a foal; the misshapen hoof made him limp at a walk, yet he galloped true and became 'the Club-footed Comet'.

Which Triple Crown winner sired fellow Triple Crown winner Omaha?

Gallant Fox sired Omaha, who swept the series five years after he did; the sire's only defeat at three came against 100-1 shot Jim Dandy in the Travers.

Which newspaper is credited with popularising the term 'Triple Crown' in 1930?

Daily Racing Form columnist Charles Hatton is credited with popularising 'Triple Crown' in his 1930 coverage, though the phrase had appeared in print as early as 1923.

Which 1964 winner was the first Canadian-bred horse to win the Kentucky Derby?

Northern Dancer was so small as a yearling that no one met his $25,000 reserve at auction; he stayed home and won the 1964 Derby in a then-record two minutes flat.

Which 1979 Derby winner set a 1:57 4/5 world record for 10 furlongs on dirt in 1980?

Spectacular Bid ran 1 1/4 miles in 1:57 4/5 in the 1980 Strub Stakes at Santa Anita; a safety pin found in his hoof on the morning of the 1979 Belmont was blamed for his lost Triple Crown.

Which 1987 Derby winner nearly fell in the stretch when a rival cut across his path?

Alysheba went almost to his knees when Bet Twice cut him off, yet recovered under Chris McCarron to win; five weeks later Bet Twice took the Belmont by 14 lengths and ended his Triple Crown bid.

Which rival denied Sunday Silence the 1989 Triple Crown by winning the Belmont?

Easy Goer, Sunday Silence's great rival, won the 1989 Belmont by eight lengths; Sunday Silence was later exported to Japan, where he led the sire list thirteen times.

For how much was Mine That Bird bought as a yearling in 2007?

Mine That Bird cost just $9,500 as a yearling; a year later, after a season that made him Canada's champion two-year-old, he was sold on for $400,000.

Which 2011 Derby winner later won the 2013 Dubai World Cup?

Animal Kingdom had never raced on dirt before he won the 2011 Derby at 21-1; two years later, aged five, he took the Dubai World Cup on Meydan's synthetic track.

Why was I'll Have Another scratched the day before the 2012 Belmont Stakes?

I'll Have Another was scratched the day before the 2012 Belmont with tendonitis and retired; owner Paul Reddam had named him for his reply when offered more cookies.

What did the 'DAP' in California Chrome's owners' partnership DAP Racing stand for?

Dumb Ass Partners was the name Steve Coburn and Perry Martin chose after hearing someone say only a dumb ass would buy California Chrome's dam, Love the Chase.

The 2016 Derby winner Nyquist was named after a player in which sport?

Owner Paul Reddam, a Detroit Red Wings fan, named Nyquist for the team's ice hockey forward Gustav Nyquist; the colt won the 2016 Derby still unbeaten.

Which jockey was aboard Country House, the 65-1 winner of the 2019 Kentucky Derby?

Flavien Prat rode Country House, who fell ill soon after the race and never ran again; Prat won the Preakness two years later.

Maximum Security finished first in which inaugural race in February 2020, only to be stripped of the win in 2024?

The Saudi Cup: Maximum Security crossed the line first in the $20 million race in Riyadh, but after trainer Jason Servis admitted doping charges he was disqualified and runner-up Midnight Bisou promoted.

Medina Spirit lost the 2021 Derby after testing positive for which steroid?

Betamethasone, an anti-inflammatory steroid, turned up in Medina Spirit's post-race test; his trainer blamed a skin ointment, but the colt was disqualified in 2022.

Before Justify in 2018, no horse since 1882 had won the Kentucky Derby without doing what?

Racing as a two-year-old had seemed essential for 136 years, the 'Curse of Apollo'; Justify made his debut only that February and had swept the Triple Crown 111 days later.

By legend, how did the 12th Earl of Derby win the right to name the race that the Kentucky Derby copies?

A coin toss, legend says, settled whether the new race took the name of Lord Derby or his guest Sir Charles Bunbury; Bunbury lost, but his colt Diomed won the first running in 1780.

Which racing operation owns 2025 Derby winner Sovereignty?

Godolphin, Sheikh Mohammed's stable, had sent out a dozen Derby runners without success before Sovereignty finally won it for them in 2025.

What flowers make up the garland given to the Kentucky Oaks winner?

Lilies: the stargazer lily became the Oaks flower in 1991, chosen for its femininity and strength, and the garland gave the race its nickname, 'Lilies for the Fillies'.

The 2020 Kentucky Derby, postponed by the pandemic, was run in which month?

September 5 was the new date; by then the Belmont had already been run, so that year the Derby was the Triple Crown's second leg, not its first.

Which owner of Secretariat did Diane Lane play in a 2010 Disney film about the colt?

Penny Chenery took charge of her ailing father's Virginia stable, and within a few years its colours had won the Derby two years running.

Which breed did Bob Baffert race and train in Arizona before switching to Thoroughbreds?

Quarter Horses: Bob Baffert grew up galloping his father's on the family ranch near Nogales, Arizona, and had a brief career as a jockey before he turned to training.

Before training horses, which sport did D. Wayne Lukas coach at a Wisconsin high school?

Basketball: D. Wayne Lukas was head coach at a high school in La Crosse, Wisconsin, before he trained horses, and racing knew him ever after as 'the Coach'.

Which jockey rode Sovereignty to win the 2025 Kentucky Derby?

Junior Alvarado rode Sovereignty past favourite Journalism on a sloppy track in the 2025 Derby, then was fined for exceeding the six-strike whip limit.

Which filly won the 2009 Kentucky Oaks by 20 lengths and then beat the colts in the Preakness?

Rachel Alexandra won the Oaks by 20¼ lengths and was sold days later; her new owners sent her against colts in the Preakness, where she became the first filly to win in 85 years.

Bill Shoemaker became the oldest jockey to win the Derby at 54 aboard which horse?

Ferdinand gave Shoemaker his fourth Derby in 1986; a year later the pair won the sport's year-end championship race by a nose, and Ferdinand was voted Horse of the Year.

Which jockey broke Bill Shoemaker's career wins record in 1999?

Laffit Pincay Jr., who had won on eight of his first 11 American mounts after arriving from Panama in 1966, passed Shoemaker's 8,833 wins at Hollywood Park in December 1999.

Which jockey rode both Whirlaway and Citation to the Triple Crown?

Eddie Arcaro won it first on Whirlaway; he got the ride on Citation only after the colt's regular jockey, his friend Al Snider, drowned on a fishing trip off the Florida Keys.

Which jockey won the Kentucky Derby three times in four years, in 2007, 2009 and 2010?

Calvin Borel was dubbed 'Bo-Rail' for hugging the inside fence, and in 2009 he did just that on a 50-1 shot, coming from last place up the rail to win.

Which jockey rode Justify to the 2018 Triple Crown at the age of 52?

Mike Smith, at 52 the oldest jockey to sweep the Triple Crown, had his closest call in the Preakness, where Justify held on by half a length.

Which horse gave Victor Espinoza his first Derby win, in 2002?

War Emblem, bought by Prince Ahmed bin Salman just three weeks before the race, took the early lead and never gave it up, handing Victor Espinoza his first Derby in 2002.

Which event opens the Kentucky Derby Festival about two weeks before the race?

Thunder Over Louisville, an air show capped by one of North America's largest fireworks displays, began in 1989 as the festival's first opening ceremony, with the fireworks set off in daylight.

What prize goes to the winner of the Kentucky Derby Festival's Great Steamboat Race?

A pair of silver antlers is kept by the winning boat until the next race; the home boat, the Belle of Louisville, lost the very first one in 1963 to the Delta Queen.

Which betting system did Churchill Downs install in 1908, when Louisville began enforcing a ban on bookmakers?

Pari-mutuel betting arrived on French machines that pooled every bet, rushed in by the track's manager; in 1911 he also cut the minimum bet from $5 to $2.

Who was the first woman to ride in the Kentucky Derby, in 1970?

Diane Crump rode Fathom to 15th in the 1970 Derby; a year earlier she had needed a police escort through a hostile crowd to become the first woman to ride in a professional US race, at Hialeah.

Which jockey, the first to win three Kentucky Derbies, entered racing's Hall of Fame in its first class in 1955?

Isaac Murphy finished last on his first mount, aged 14, then won the Derby on Buchanan, Riley and Kingman and, by later counts, about a third of all his races.

After winning the 1901 and 1902 Derbies, Jimmy Winkfield found success in which country?

Jimmy Winkfield became Russia's champion jockey; when the revolution came in 1917 he helped lead a herd of racehorses on a 1,000-mile escape from Odessa.

Which cosmetics tycoon's stable owned Jet Pilot, the 1947 Kentucky Derby winner?

Elizabeth Arden's Maine Chance Farm had lost 22 horses in a barn fire a year earlier; Jet Pilot escaped only because he had been shipped to Churchill Downs.

What is the maximum number of horses allowed to start in the Kentucky Derby?

20 has been the limit since 1975, the year after a record 23 horses crowded into the 100th running.

Which filly won the 1980 Kentucky Derby?

Genuine Risk became only the second filly to win the Derby, then ran second in a stormy Preakness: her jockey claimed foul against the winner, Codex, but the stewards let the result stand.

Which 2006 Derby winner shattered a hind leg in the Preakness two weeks later?

Barbaro, unbeaten when he won the 2006 Derby by 6½ lengths, broke his right hind leg in the Preakness; after eight months of treatment he was euthanised in January 2007.

Which trainer won the Derby with both Strike the Gold in 1991 and Go for Gin in 1994?

Nick Zito trained both winners and later turned spoiler: his longshot Birdstone ran down an unbeaten Derby winner in the 2004 Belmont to end a Triple Crown bid.

Which jockey dismounted to cradle Charismatic's fractured leg after the 1999 Belmont?

Chris Antley jumped off and cradled Charismatic's fractured left foreleg after the 1999 Belmont, likely saving the colt's life; Charismatic was nevertheless voted Horse of the Year.

Which 2007 Derby winner had taken the Breeders' Cup Juvenile by a record margin?

Street Sense won the 2006 Breeders' Cup Juvenile by a record 10 lengths; no winner of that race had ever gone on to take the Derby until he did so the following May.

Which veteran Phipps trainer won the 2013 Derby with Orb?

Shug McGaughey, who had trained for the Phipps family since 1986, won his first Derby when Orb came from the rear of the field on a sloppy track; he called it the day he had always dreamed of.

Which 2008 winner was the first since 1929 to win the Derby from post position 20?

Big Brown won from the far outside post, last done by Clyde Van Dusen in 1929, and added the Preakness; in the Belmont he was eased and failed to finish.

Which 1998 Derby winner, nicknamed 'The Fish', lost the Belmont by just four inches?

Real Quiet, called 'The Fish' for his narrow frame, had sold for $17,000 as a yearling because of crooked knees; Victory Gallop caught him by a nose in the 1998 Belmont.

Which Kentucky retirement farm took in Silver Charm on his 2014 return from Japan?

Old Friends Farm at Georgetown took Silver Charm in after the Lewis family, who had raced him, helped arrange and pay for his return from stud duty in Japan.

Which jockey rode Thunder Gulch to victory at 25-1 in the 1995 Derby?

Gary Stevens won on Thunder Gulch, one of three runners his trainer sent out in the 1995 Derby; two weeks later stablemate Timber Country turned the tables on him in the Preakness.

Which philanthropist's Rokeby Stables owned 1993 Derby winner Sea Hero?

Paul Mellon's Rokeby Stables bred Sea Hero in Virginia; the colt also earned a $1 million Triple Crown series bonus, which Mellon gave away to equine research.

Which odds-on favourite did Lil E. Tee upset in the 1992 Kentucky Derby?

Arazi, hyped as a wonder horse after his Breeders' Cup Juvenile win, swept up to the leaders on the turn and then tired to finish eighth; Lil E. Tee, named for the film alien E.T., won under Pat Day.

Which sire produced both Derby winners Donerail and Exterminator?

McGee, a modestly regarded stallion standing in Kentucky, sired both Donerail and Exterminator; the latter was gelded young because he was awkward and coarse-looking.

What is a racehorse called before its first win, as 1933 Derby winner Brokers Tip was?

A maiden until Derby day, Brokers Tip never won another race; his 'Fighting Finish' is famous because the two leading jockeys fought each other on horseback down the stretch.

The Derby winner wears roses; which flower is the Preakness winner's blanket named for?

Black-eyed Susans don't bloom until weeks after the race, so the blanket has never used them: daisies were once painted to look the part, and chrysanthemums stand in today.

What is the Kentucky Derby winner's trophy made of?

Gold, mostly 14-karat: its decorative horseshoe pointed down until 1999, when it was turned to point up in deference to racing lore about luck.

Which trainer won the 2025 Kentucky Derby with Sovereignty, his second Derby win?

Bill Mott then skipped the Preakness with Sovereignty, giving up any chance of the Triple Crown, and the rested colt went on to win the Belmont.

Which two horses gave Todd Pletcher his first two Kentucky Derby wins?

Super Saver and Always Dreaming won in 2010 and 2017; before Super Saver, Todd Pletcher had sent out 24 Derby runners without a win.

Which filly gave Kenny McPeek the 2024 Kentucky Oaks alongside Mystik Dan's Derby?

Thorpedo Anna's Oaks, a day before Mystik Dan's Derby, made Kenny McPeek the first trainer since 1952 to win both in one year; she later took on colts in the Travers, lost by a head and was still voted Horse of the Year.

Who became the first woman jockey to win the Kentucky Oaks, in 2012?

Rosie Napravnik won the 2012 Oaks on Believe You Can and the 2014 running on Untapable; later that year, after another big win on Untapable, she announced she was pregnant and stepped away from riding.

Which bourbon brand became the Kentucky Derby's presenting sponsor in 2018, taking over from a Louisville fast-food company?

Woodford Reserve is made by Louisville's Brown-Forman and took the sponsorship in 2018 from a Louisville fast-food company that had held it since 2006, so the Derby's title stayed in its home town.

What traditional command from the Paddock Judge tells jockeys to mount their horses before the race?

'Riders up!' is the Paddock Judge's traditional order to mount, after which each jockey gets a leg up; since 2012 a celebrity guest has delivered the call.

Which racing phrase describes leading from start to finish, as Winning Colors did in the 1988 Derby?

Wire-to-wire is how the filly Winning Colors won in 1988: she broke fast, went straight to the lead and held off Forty Niner's late charge by a neck.

Which writer's 1970 article on the Kentucky Derby, illustrated by Ralph Steadman, launched gonzo journalism?

Hunter S. Thompson and Steadman could not even see the race from where they stood, so the Scanlan's Monthly piece skewered the partying crowd instead.

Which ornament on the Kentucky Derby winner's trophy was turned upside down for the 125th running in 1999?

The horseshoe had pointed down on every trophy since 1924, and racing superstition holds that a shoe hung that way lets all the luck run out.

Giacomo, the 50-1 winner of the 2005 Kentucky Derby, was named after the son of which rock star?

Sting's son gave his name to the gray colt, whose owner Jerry Moss co-founded A&M Records with trumpeter Herb Alpert.

Which bugle tune is sounded at Churchill Downs to summon the Kentucky Derby horses onto the track?

Call to the Post is the bugle call First Call under its racetrack name. It tells the mounts to leave the paddock and begin the parade to the starting gate.

Which nickname is given to the box seats where celebrities watch the Kentucky Derby?

Millionaire's Row draws the rich, the famous and the well-connected, while the infield crowd below pays general admission and can barely see the race.

The Kentucky Derby is open only to three-year-old horses of which breed, developed in England for racing?

Thoroughbred horses run the Derby at three, so each gets exactly one chance to win it. The breed arose when English mares were crossed with imported Arabian, Barb and Turkoman stallions.

Which nut is baked with chocolate into Derby-Pie, the trademarked Kentucky dessert first made in 1954?

Walnuts and chocolate fill the pie, whose recipe is a family secret. Kern's Kitchen has filed more than 25 lawsuits to protect the Derby-Pie name.

Funny Cide in 2003 became the first Kentucky Derby winner in 74 years to be which type of horse?

A gelding had not won since Clyde Van Dusen in 1929. Trainer Barclay Tagg had bought Funny Cide for $75,000 on behalf of Sackatoga Stable.

Which network carried the first national television coverage of the Kentucky Derby, on May 3, 1952?

CBS took the race nationwide through its affiliate WHAS-TV, three years after a local station first televised the Derby for viewers in its home city.

Canonero II, the shock winner of the 1971 Kentucky Derby, had been shipped to the race from which country?

Venezuela became his home after he sold as a yearling for just $1,200, and he went on to win the second leg of the Triple Crown as well.

The 2018 Kentucky Derby broke a Derby Day record that had stood since 1918 for which of these?

Total rainfall passed 2.8 inches by race time, beating the 2.31 inches of 1918, yet 157,813 people came to watch anyway.

The 144th Kentucky Derby, held in 2018, was run on the date of which annual celebration?

Cinco de Mayo, May 5, was the date. The race is normally run within the first seven days of May, so the two sometimes coincide.

What color is the coat of the 2018 Kentucky Derby winner, a massive colt with a large white blaze?

Chestnut and huge even for a racehorse, he stood 16.3 hands at the withers and weighed well over 1,200 pounds during his Triple Crown run.

Which honor did the 2018 Kentucky Derby winner take by 191 votes to 51 over Accelerate?

Horse of the Year went to a colt who had already been retired for six months, after a career of only six races run in under four months.

What ended the racing career of the 2018 Kentucky Derby winner less than three months after the race?

An ankle problem, a filling in his left front leg that went down and then came back, led to his retirement on July 25, 2018.

Which Asian racing group owned a quarter of the 2018 Kentucky Derby winner alongside WinStar?

China Horse Club took 25 per cent when the colt was bought as a yearling for $500,000, with WinStar holding 60 per cent.

Employees of which billionaire investor's firm ran SF Racing, a partner in the 2018 Kentucky Derby winner?

George Soros's staff held 15 per cent of the colt through SF Racing, the smallest share in the three-way partnership that bought him as a yearling.

Which stallion, who died in 2015 at the age of eleven, sired the winner of the 2018 Kentucky Derby?

Scat Daddy died just as his value was soaring: his stud fee, $35,000 for this mating, had been due to rise to $100,000.

Which Irish-trained colt romped in the 2018 UAE Derby but finished last in that year's Kentucky Derby?

Mendelssohn was hit hard just after the start and eased to the finish. He had cost $3 million as North America's most expensive auction yearling of 2016.

At which auction house's September yearling sale was the 2018 Kentucky Derby winner bought for $500,000?

Keeneland was also where he was first sent to be trained, by Rodolphe Brisset, before a pulled muscle earned him time off to grow into his frame.

Which 65-1 longshot was awarded the 2019 Kentucky Derby after stewards demoted the first horse home?

Country House was at the time the second-longest-priced winner in the race's history, even though the incident on the final turn had done him no material harm.

What became of the racing career of the colt promoted to first place in the 2019 Kentucky Derby?

He never raced again: a leg infection that summer led to laminitis, and he had already become the first Derby winner since 1996 to miss the next Triple Crown race.

Which colt, cut off by Maximum Security in the 2019 Derby, won the next Triple Crown race two weeks later?

War of Will was the horse most directly cut off. His trainer, Mark Casse, said he would have lodged an objection himself had the colt finished in the money.

Which jockey was suspended for fifteen days for failing to keep Maximum Security straight in the 2019 Derby?

Luis Saez was cited for failing to control his mount. He had steered the colt back toward the rail almost at once, bumping another rival on the way.

Which pre-race favorite was scratched from the 2019 Kentucky Derby with an entrapped epiglottis?

Omaha Beach had won the Arkansas Derby and was the 4-1 choice until the throat condition, which impaired his breathing, ruled him out.

Which trainer of Maximum Security was sentenced in 2023 to four years in prison for doping horses?

Jason Servis was indicted in March 2020, ten months after the Derby, and the colt was moved to another trainer's barn.

Master Fencer reached the 2019 Kentucky Derby through which country's own qualifying series?

Japan's top three qualifiers turned the invitation down, so it passed to fourth-placed Master Fencer, the first Japanese-bred horse to take that route.

Maximum Security, first past the wire in the 2019 Derby, had begun his career in which kind of contest?

A maiden claiming race meant any licensed owner could have bought him for $16,000 that December day, and nobody put in a claim.

What did Maximum Security's jockey say made the colt swerve on the final turn of the 2019 Kentucky Derby?

Noise from the crowd in the infield made him shy, the rider said, but the stewards held him responsible for failing to keep a straight course.

What did Maximum Security's owners do ten days after stewards took the 2019 Derby away from their colt?

They sued in federal court to restore the win, but the case was thrown out that November because stewards' rulings on fouls are final.

At a Kentucky Derby betting window, what must a trifecta ticket predict before it pays out?

Top three in exact order is the task, which is why many bettors 'box' three horses, buying all six possible finishing arrangements.

A 'show' bet on a Kentucky Derby runner pays out if the horse finishes where?

First, second or third all cash the ticket. Strictly, to show is to run third, but the bet also pays when the horse does better.

A Kentucky Derby bettor who backs one horse to win, place and show is making which kind of wager?

Across the board is really three separate bets on the same horse, so a $2 ticket costs $6 and a winner collects on all three.

Which Kentucky Derby wager, also called a perfecta, asks for the top two finishers in the right order?

Exacta tickets must name the pair in the order they finish. A quinella, by contrast, pays whichever way round the same two horses come home.

Which Kentucky Derby wager requires picking the top four finishers of the race in the correct sequence?

Superfecta payouts dwarf the trifecta's because a fourth horse must be placed too. In Australia the same bet is usually called a First Four.

Under which system, restored at Churchill Downs in 1908, do Kentucky Derby bettors wager against each other?

Parimutuel betting pools all the money and splits it among the winners, so nobody is betting against the house. Joseph Oller devised it in 1867.

What name is given to the approximate odds set for each Kentucky Derby runner before wagering begins?

Morning line odds are only an oddsmaker's forecast. Once the windows open, the money actually bet on each horse sets the real price.

In racetrack slang, what one-word name is given to the betting favorite in a race like the Kentucky Derby?

Chalk is the horse at the lowest win odds, and a bettor who routinely backs favorites is known as a chalk player.

Which wager, North America's first 'exotic' bet, requires picking the winners of two consecutive races?

Daily double betting began at Connaught Park near Ottawa, and tracks soon attached it to the first two races of the day to draw spectators in early.

In racing, what name is given to the total amount of money wagered on a race such as the Kentucky Derby?

Handle can be counted for one race, a full day's card, a whole meeting or a year, and it takes in every betting pool at the track.