1888: three-year-old season
Although Friar’s Balsam was perceived as by far the best colt of his generation, Ayrshire who had thrived over the winter was regarded by some observers as a potential Derby winner. Ayrshire began his three-year-old season in the Riddlesworth Stakes at Newmarket, which he won by twenty lengths from his only opponent. In the 2000 Guineas on Ayrshire was started at 8/1 in a field of six but Friar’s Balsam was considered such a certainty that many bookmakers refused to accept bets on the favourite. Friar’s Balsam was, however, suffering from an undetected mouth abscess which burst during the race, causing him to choke on “blood and matter”. Ayrshire, ridden by the fifty-five-year-old veteran John Osborne, tracked his stable companion Johnny Morgan before moving into the lead a furlong out and winning “in a common canter” by two lengths. Johnny Morgan held off Orbit for second, while Friar’s Balsam finished distressed in fifth. Immediately following the race Ayrshire’s price for the Derby was cut from 7/1 to 6/4.
At Epsom on 30 May Ayrshire started 5/6 favourite for the Derby in a field of nine, in front of a crowd estimated at 150,000. His owner, the Duke of Portland watched the race from the Royal Box in the company of the Prince of Wales. Ayrshire broke quickly but was then held up and settled in fourth by his rider Fred Barrett. Van Dieman’s Land went to the front at half way and held a clear lead turning into the straight as Barrett moved Ayrshire into contention. Two furlongs from the finish, Ayrshire took the lead from Orbit and Van Dieman’s Land. He quickly went clear and held off the strong late challenge of Crowberry to win by two lengths, despite swerving near the finish. The official time of 2:43 equalled the race record, although the Sporting Life timed the winner at 2:42.2.
Shortly after the Derby Ayrshire was found to be lame as a result of a splint and was off the racecourse for more than three months. He started favourite for the St Leger on 12 September against fifteen opponents, with his biggest danger appearing to be Seabreeze, who had won The Oaks. Ayrshire raced prominently and was moved up to challenge Seabreeze for the lead early in the straight. He soon weakened however, suggesting a lack of stamina, and dropped back to finish sixth, as the filly won easily. Ten days later Ayrshire ran over the much shorter distance of seven furlongs in the £10,000 Lancashire Plate at Manchester Racecourse. Looking fitter than he had done at Doncaster, he produced a much better effort, leading the field of twenty-four runners until headed by Seabreeze well inside the final furlong. Ayrshire "struggled gamely" but was beaten three quarters of a length in a finish of "intense excitement." Ayrshire reappeared at Newmarket three days later for his final start of the year, and won the Great Foal Plate, beating the Doncaster Cup winner Grafton.