Racing career
1886: two-year-old season
On 8 June Enterprise made his racecourse debut in the New Stakes at Royal Ascot. He was ridden by George Barrett and won at odds of 100/12 upsetting the hot favourite Freedom.[5][6] He was expected to follow up in the Royal Plate at Windsor Racecourse but was defeated by George Chetwynd's colt Stetchworth.[7] At Newmarket Racecourse on 6 July, the colt started 2/1 joint-favourite for the July Stakes. Ridden by Fred Archer he took the lead soon after the start and despite hanging left just inside the last quarter mile he won "easily" by four lengths from Hugo.[8] On 13 October at Newmarket Enterprise finished second to Lord Calthorpe's colt Florentine in the Middle Park Plate, a race for which he had been regarded as a near certainty and started at odds of 1/7.[9][10] In the Dewhurst Plate two weeks later over seven furlongs at the same track he started 7/2 second favourite behind Phil. After disputing the lead for most of the way he appeared to "cut it" (give up) in the final furlong and was beaten three lengths into second place by the Duke of Beaufort's filly Reve d'Or, a 20/1 outsider.[11]
At the end of year Fred Archer reportedly said "If he hadn't had a touch of the white feather, Enterprise would be a second Ormonde".[12]
1887: three-year-old season
On 27 April 1887, Enterprise, ridden by Tom Cannon started the 2/1 favourite for the 79th running of the 200 Guineas over the Rowley Mile. Phil (10/1), Florentine (10/1) and Hugo (20/1) were again in opposition but the best fancied of his opponents were Eglamore, Grandison (Windsor Castle Stakes) and Lovegold. Enterprise started well and as the field entered the last quarter mile he moved into third place behind Eglamore and Phil, with the three colts drawing well clear of the rest. Racing in the centre of the trio, he gained the advantage inside the final furlong and won "rather easily"[13] in "capital style"[14] by half a length from Phil with Eglamore the same distance away in third place.[15] Despite the close finish, Cannon always appeared to be in control of the race ensuring that Baird and his associates collected very large sums in winning bets.[16] The winning time of 1:45.6 constituted a new record for the race.[17]
Enterprise was strongly fancied for the Epsom Derby, being quoted at odds of 9/4 a week before the race.[18] When engaged in training on the Limekilns gallop the colt reportedly took fright, jumped a hedge onto a road and had to be retrieved from an adjacent field. Although he "wrenched"[19] himself, the initial prognostications were good, but he was subsequently withdrawn from the contest.[20]
1888: four-year-old season
On 27 July 1888 Enterprise started the 100/12 third choice in the betting for the Eclipse Stakes at Sandown Park but finished sixth behind the Duke of Westminster's colt Orbit.[21] On 22 September the colt started a 33/1 outsider for the £11,000 Lancashire Plate over seven furlongs at Manchester Racecourse and came home unplaced behind Seabreeze.[22]