[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.
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.
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.
[20] 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.