Secretariat holds the record for the fastest Kentucky Derby ever at 1:59.40, which is also the track record for the 1 1/4 mile distance at Churchill Downs. He went on to win the Triple Crown and was named Horse of the Year as well as Champion 3-year-old for 1973. He is still considered by many to be the best thoroughbred ever to race. 2013 is the 40th anniversary of Secretariat’s Kentucky Derby.
Because the question has been asked, I will put a note there that Sham, who ran 2nd behind Secretariat, also ran faster than many winners did, but since he did not win he is not included on this list as it is strictly for the fastest winning times.
Monarchos surprised everyone when he won the Derby in 1:59.97 to become the second fastest Derby winner in history in 2001. He rallied from 13th early on to win by 4 3/4 lengths. He was unplaced in the Preakness and 3rd in the Belmont Stakes. He currently stands at stud at Claiborne Farm in Lexington, Kentucky.
Northern Dancer has the third fastest Kentucky Derby win of all time at 2:00 flat. The Canadian-bred had an awesome 3-year-old season with wins in the Flamingo Stakes, Florida Derby, Blue Grass Stakes, Preakness, and Queen’s Plate in addition to his win in the Kentucky Derby. He finished 3rd in the Belmont and was retired soon after, becoming of the most influential sires of thoroughbreds ever.
Spend a Buck won his Kentucky Derby in wire-to-wire fashion, coming home 5 1/4 lengths in front with a final time of 2:00.20 for the 4th fastest Derby win ever. He went on to be named Horse of the Year for 1985 aa well as Champion 3-year-old Colt. He was a bit controversial as he skipped the rest of the Triple Crown to run in the Jersey Derby instead because of a $2 million bonus he was eligible for because of his win in the Garden State Stakes, he of course won the Jersey Derby and collected the bonus.
Decidedly won in 1962 in 2:00.40 by 2 1/4 lengths at odds of 8.70-1, the 5th fastest winner in the history of the race. The gray colt was sired by Determine who also won the Derby in 1954. He raced through age 5 and retired with a record of 11 wins, 9 seconds, and 4 thirds in 43 starts with earnings of $318,989.
Proud Clarion was a huge upset at 30-1 odds when he won the Kentucky Derby in 1967 in a final time of 2:00.60, the 6th fastest ever. He went on to be 3rd in the Preakness and was unplaced in the Belmont Stakes.
Grindstone rallied from 15th to win by a nose in 1996 with a final time of 2:01.06 for the 7th fastest Derby win ever. One of four Kentucky Derby winners trained by the legendary D. Wayne Lukas, he was retired soon after the race due to injury. He stands at stud at Overbrook Farm in Kentucky where he was also bred.
Fusaichi Pegasus rallied from 15th to win the 2000 Kentucky Derby by 1 1/2 lengths in a final time of 2:01.12 for the 8th fasted Derby win of all time. He was also the first favorite to win in 20 years and the only Derby winner to be purchased at auction for over $1 million. He was 2nd in the Preakness and skipped the Belmont Stakes. He tried to come back in the Breeders’ Cup Classic that fall and was unplaced then retired. He stands at stud at Ashford Stud in Kentucky.
War Emblem won the Kentucky Derby in 2002 wire-to-wire by 4 lengths in a final time of 2:01.13 for the 9th fastest Derby win ever. War Emblem went on to win the Preakness and was highly touted as the next Triple Crown winner, but disappointed in the Belmont Stakes where he was 8th after going to his knees at the start.
Funny Cide in 2003 owns the 10th fastest Derby win at 2:01.19. He became the first New York-bred to win the Derby and was the first gelding since 1929 to win. He went on to win the Preakness and was 3rd in at very muddy Belmont Stakes. He enjoyed being at the track and raced until age 7 when he was retired to become a stable pony for his trainer Barclay Tagg.