ESPN Classic looks back at some of the most memorable moments in the Kentucky Derby's history.

May 9, 1914
Old Rosebud gives a record-setting performance in becoming the first gelding in 26 years to win the Kentucky Derby.

In the field of seven 3-year-olds, Old Rosebud jumps to the lead. On the backstretch, Hodge, also a gelding, tries to move up. But Old Rosebud, under the urging of jockey John McCabe. responds to the challenge and increases his lead to eight lengths at the finish over Hodge.

With his wire-to-wire triumph, Old Rosebud sets Derby and track records for the 1¼-mile race at Churchill Downs with his time of 2:03 2/5 over a track not considered fast. Old Rosebud, the 4-5 favorite, is trained by F.D. Weir and owned by H.C. Applegate & Co. of Louisville.

The Derby record will last 17 years, until Twenty Grand wins the race in 2:01 4/5 in 1931.

May 1, 1948
With only six horses, the Kentucky Derby has its smallest field since 1907. Few believe Citation can be beaten. There is only straight betting on the race, and Citation and Calumet Farm stablemate Coaltown are the 2-5 favorites.

Coaltown leads by eight lengths in the backstretch, but Citation, with Eddie Arcaro aboard, catches him as they head for the homestretch. Then Citation pulls away to a 3.5-length victory over Coaltown in 2:05 2/5 before a crowd of close to 100,000 in Louisville. He earns $83,400 of the $111,450 purse for Calumet Farms and $2.80 to his backers.

Arcaro is the first jockey to win four Kentucky Derbies. Arcaro got the ride on Citation after the horse's regular rider, Al Snider, went boating and never returned, presumed lost at sea. Arcaro gives half of his Derby winnings to Snider's widow. While Ben Jones ties the record for trainers by saddling his fourth Derby winner, it is his son Jimmy who does most of the work with Citation.

Citation will go on to win the Preakness and Belmont, becoming the fourth horse to win the Triple Crown in the forties. He will be the last Triple Crown winner for 25 years, until Secretariat in 1973.

May 4, 1957
A gallant man's mistake costs Gallant Man in the Kentucky Derby.

Legendary jockey Willie Shoemaker, aboard English-bred Gallant Man, mistakes the 16th pole for the finish line and momentarily stands up in his saddle. As he does, Willie Hartack continues to drive 8-1 shot Iron Liege. Shoemaker quickly resumes driving his mount, but Gallant Man is unable to catch Iron Liege, losing by the thinnest of noses in one of the most controversial derbies ever.

"(Shoemaker's mistake) undoubtedly cost him the race," says Lincoln Plaut, presiding steward.

Ironically, Ralph Lowe, the owner of Gallant Man, told Churchill Downs track s superintendents before the race that he had dreamed last night that his jockey "stood up in the stirrups" on the colt. Unfortunately for Lowe, his dream becomes a real-life nightmare for Shoemaker.

Iron Liege is not even considered Calumet Farm's best three-year-old. That honor goes to General Duke, who is scratched because of an injury a few minutes before the pre-Derby betting begins today. With Hartack winning his first Derby, the "second-string" Iron Liege pays $18.80 to win.

May 5, 1973
As a two-year-old last year, Secretariat was named Horse of the Year, an honor that rarely goes to such a young colt. But some doubted his "superstar" tag after he finished third in the Wood Memorial, his last performance before today's Kentucky Derby.

Along with stablemate Angle Light, who won the Wood, they are 3-2 Derby favorites. Secretariat shows again why he is considered the best colt in many generations. Getting off far back in the field of 13, Secretariat bursts into contention in the stretch turn.

Big Red then gives a breath-taking performance, blazing the final quarter in 23 1/5 seconds. Secretariat, with Ron Turcotte aboard, finishes 2 1/2 lengths ahead of Sham in winning in 1:59 2/5, the first horse to ever break two minutes in the Derby. The son of 1957 Preakness winner Bold Ruler pays $5 to win. Secretariat will go on to win the Preakness and Belmont, becoming the first horse in 25 years to win the Triple Crown.

May 6, 1978
Though Affirmed had beaten Alydar in four of their six meetings as 2-year-olds last year, he's only second choice at 9-5 at today's Kentucky Derby to the 6-5 Calumet Farm favorite. Aboard Affirmed is 18-year-old Steve Cauthen, who grew up 80 miles from Churchill Downs in Walton, Ky.

In his first Derby ride, the teenager follows trainer Laz Barrera's instructions, keeping Affirmed close to the lead for most of the race before getting into high gear. Affirmed passes Believe It with about a quarter mile to go and holds off the charging Alydar in the final eighth of a mile. Affirmed wins by a length over the favorite in 2:01 1/5 and pays $5.60 for a $2 bet.

"Steve rode the horse perfect," says Barrera. "I think he rode a long time ago and came with 80 years experience. What do you call it? Reincarnation?"

Cauthen will ride Affirmed to the Triple Crown, with Alydar finishing second in both the Preakness and Belmont.

May 3, 1986
The year 1986 is a very good one for athletes in the twilight of their sports. Just last month, Jack Nicklaus, at 46, won the Masters. Today, Willie Shoemaker, at 54, gives a superb ride to bring home long shot Ferdinand first in the Kentucky Derby.

Shoe steers Ferdinand, a son of the English Triple Crown winner Nijinsky II, through heavy traffic from last place after a half mile to first at the finish, 2 1/4 lengths in front of Bold Arrangement. Running the 1 1/4 miles in 2:02 4/5, Ferdinand, who had won only two of his nine races, pays $37.40 for $2 to win. The race is a sentimental triumph for Shoemaker, who becomes the oldest jockey to win the Kentucky Derby. It is his fourth Derby victory, but the last one was 21 years ago, aboard Lucky Debonair.

"This Derby win is the best," says Shoemaker. "Like good old Kentucky bourbon, I improve with age."

May 7, 1988
Wayne Lukas heard the critics who thought that the trainer should have raced his filly against others of her sex in yesterday's Oaks rather than running against the boys in today's Kentucky Derby. But Lukas, who had lost with his first 12 Derby horses, is glowing after the race, having the winning ticket with Winning Colors.

The colt-sized, roan-gray horse becomes the third filly to win the Derby. Under Gary Stevens, she moves to the lead quickly, cruising ahead of her 16 male challengers, takes a lead of 3+ lengths in the stretch and holds off a persistent charge by Forty Niner to win by a neck in a solid 2:02 1/5. Her wire-to-wire victory is worth $8.80 for those who bet $2 on her.

In winning the closest Derby in 19 years, Winning Colors joins Regret (1915) and Genuine Risk (1980) as the only fillies to smell the roses at the Derby.

"I'd like to salute all the women of America," owner Gene Klein says at the trophy presentation. "This one's for you gals."