2000: three-year-old season Medicean did not race as a two-year-old: when he arrived at Stoute's stable he was described as resembling "two boards put together" and underwent an operation after developing
colic. On 1 June he was sent north to
Ayr Racecourse for another minor stakes and won "readily" from five opponents. Less than three weeks later, Medicean was moved up sharply in class for the
Group One St James's Palace Stakes at
Royal Ascot. Starting a 16/1 outsider, he exceeded expectations by finishing third, less than a length behind the winner
Giant's Causeway. On his next appearance, the colt moved up in distance for the John Smith's Cup, an all-aged
handicap race over ten and a half
furlongs at
York Racecourse. Carrying a weight of 112
pounds he started the 5/2 favourite, despite Stoute's concerns about the soft ground, but made no impression in the race and finished fourteenth of the twenty-two runners. In his three remaining races of the year, Medicean returned to
weight-for-age races and the one mile distance. On 2 August he finished third behind the joint-favourites Giant's Causeway and
Dansili in the Group One
Sussex Stakes at
Goodwood Racecourse, beaten two and a quarter lengths by the winner. At the end of the month, he returned to Goodwood for the Celebration Mile in which he was opposed by the
Jersey Stakes winner Observatory and by Bachir, who had defeated Giant's Causeway in the
Irish 1,000 Guineas. Ridden by the forty-eight-year-old
Pat Eddery, Medicean tracked Bachir before taking the lead three furlongs from the finish. Under a hard ride from Eddery, Medicean recorded his first important success, beating Observatory by a length. On his final race as a three-year-old, he finished fourth behind Observatory, Giant's Causeway and Best of the Bests in the
Queen Elizabeth II Stakes at Ascot in September.
2001: four-year-old season Medicean remained in training as a four-year-old in 2001, when he was ridden in all of his races by
Kieren Fallon. On his first appearance of the year he contested the Group One Lockinge Stakes over one mile at
Newbury Racecourse on 19 May. Fallon restrained the colt towards the rear of the seven runner field before making his challenge in the final furlong. Medicean caught the leaders in the final strides and won in a three-way
photo-finish from Warningford and Swallow Flight. Explaining his decision to wait until the last moment to deliver his challenge, Fallon said "He's a horse who needs to be ridden that way. When he hits the front he thinks he's done enough. It was a surprise that he won, because a lot of our horses are just needing the run. I thought he would have, but his ability got him through it." At Royal Ascot in June the colt started at odds of 11/2 for the
Queen Anne Stakes (then a Group Two race) in which he carried a five-pound weight penalty following his Group One win. He took the lead two furlongs from the finish and was driven out by Fallon to win by a length from Swallow Flight. On 7 July, Medicean was one of eight horses to contest the 104th running of the Eclipse Stakes at Sandown. His opponents included
Grandera,
Tobougg, Black Minnaloushe (winner of the
Irish 2,000 Guineas and St James's Palace Stakes) and Endless Hall (winner of the
Singapore Airlines International Cup). Racing over ten furlongs for the second time in his racing career, Medicean was held up by Fallon at the back of the field as a very strong pace was set by Broche and Darwin. Medicean moved into contention in the straight, but came under pressure and appeared to be struggling before rallying in the closing stages to win by half a length from Grandera, with Bach in third place. At
York Racecourse in August Medicean started 3/1 second favourite for the
International Stakes over furlongs and finished third of the eight runners, eight lengths behind the winner
Sakhee. Medicean was expected to race again in autumn, with the
Champion Stakes and the
Breeders' Cup Mile regarded as potential targets. In October, he sustained an injury to his right foreleg in training and was retired from racing. Stoute paid tribute to the colt on his retirement, saying: "He was a model of consistency throughout his career and always showed great courage. That's exactly what he showed when winning the Eclipse, but I felt his performance in the Queen Anne with a penalty was outstanding." ==Stud record==