Monarchos raced twice as a two-year-old, finishing eighth at
Keeneland Racetrack on October 7, and third at
Churchill Downs on November 24. He made a winning three-year-old debut when taking a minor race at
Gulfstream Park in January 2001 and followed up with a win in an
allowance race in February. He established himself as a contender for the Kentucky Derby with his run in the
Florida Derby in March. Ridden by
Jorge Chavez, he won by four and a half
lengths from Outofthebox and Invisible Ink. Chavez was impressed by the performance, saying that "when I asked him, he just exploded."
Bill Nack, writing in
Sports Illustrated, was equally enthusiastic, calling the win "electrifying" and drawing comparisons with other famous grays such as
Spectacular Bid and
Holy Bull. At
Churchill Downs on 5 May, Monarchos was the 10.5/1 fourth choice in the betting for the Derby. After being bumped at the start, he made steady progress on the outside and turned into the straight in sixth place. Chavez sent the gray colt to the lead a furlong from the finish, and Monarchos pulled clear to win by almost five lengths from Invisible Ink, with Congaree third and the favored
Point Given fifth. Monarchos' winning time was 1:59.97 for miles, becoming only the third horse in Derby history to finish the race in under 2 minutes, joining 1973
Triple Crown winner
Secretariat, who ran 1:59 , and his runner up,
Sham, who ran 1:59 (at that time, the Derby was timed to the fifth of a second rather than to the hundredth of a second). As of 2025, no horse since Monarchos has broken the 2-minute barrier at the Derby. In the Preakness Stakes, Monarchos was outrun in the early stages and finished sixth of the eleven runners behind Point Given. In the Belmont Stakes, he finished third, more than thirteen lengths behind the winner, Point Given. Some time after the race, it was discovered that Monarchos had sustained a hairline fracture to his right knee, which ruled him out for the rest of the season. ==Stud career==