As a yearling, Milan was sent to the Tattersalls sales at Newmarket, where he was bought for 650,000 guineas by the bloodstock agent Dermot "Demi" O'Byrne on behalf of the Coolmore organisation.

Milan tracked the leaders before moving into the lead a furlong from the finish and quickened clear to win "easily"[4] by three and a half lengths from his stable companion Leopard Spot.

[5] In the Prix du Jockey Club at Chantilly in June he was poorly drawn and stumbled exiting the stalls before finishing "powerfully"[6] to take fifth place behind Anabaa Blue.

Later in June, Milan started favourite for the King Edward VII Stakes at Royal Ascot but finished fourth of the twelve runners behind Storming Home.

[8] Aidan O'Brien explained that the colt had been given a break since things had happened "a bit quick for him" in France and at Ascot, and that he had been looking fresh in training.

Milan was held up at the rear of the field before making steady progress but appeared to be boxed in on the rail[10] before being switched to the outside in the straight.

He took the lead a furlong from the finish and pulled clear of the field with what the BBC described as an "incredible burst of speed"[11] to win by five lengths from Demophilos and Mr Combustible.

[14] The final start of Milan's three-year-old season saw him race outside Europe for the only time as he was sent to Belmont Park for the Breeders' Cup Turf.

Milan was retired to stand for his owners' Coolmore Stud organisation and was primarily marketed as a National Hunt stallion.