[1] As a yearling he was sent by his breeders to the Tattersalls Houghton sales in September 1995 where he was bought for 600,000 guineas by the bloodstock agent Dermot "Demi" O'Byrne on behalf of John Magnier's Coolmore organisation.

[5] Three weeks later he won a similar event at Kempton taking the lead two furlongs out and accelerating away from the other runners to beat Falak by five lengths.

[7] On his first appearance of 1997 Entrepreneur ran in the classic 2000 Guineas at Newmarket on 3 May for which he was made 11/2 second favourite despite never having previously contested a Group race.

[10] Entrepreneur ran against twelve opponents in the Derby at Epsom on 7 June and started the 4/6 favourite with Silver Patriarch being the second choice in the betting at 6/1.

He appeared to have every chance in the straight but came under pressure and was unable to reach the lead before finishing fourth behind Benny the Dip, Silver Patriarch and Romanov, beaten more than eight and a half lengths.

[11] Following his defeat in the Derby, Entrepreneur was off the racecourse for more than three months before returning in the Queen Elizabeth II Stakes over one mile at Ascot on 27 September.