On his three-year-old debut, High Top was sent to Yorkshire to contest the Classic Trial at Thirsk Racecourse. he led from the start and won by five lengths from My Brief, with the leading filly Waterloo two lengths further back in third. With both Crowned Prince and Sharpen Up failing in their respective trials, High Top was Van Cutsem's sole representative in the 2000 Guineas over the Rowley Mile course at Newmarket on 29 April. With Carson again in the saddle, he started the 85/40 favourite against eleven opponents, his form having been boosted by the success of Waterloo in the 1000 Guineas two days earlier. High Top led from the start and went well clear approaching the final furlong. In the closing stages the Irish-trained colt Roberto emerged as a challenger, but the favourite was driven out by Carson to win by half a length, with a gap of six lengths back to Sun Prince in third. The colt's success was a first classic win for both Carson and Van Cutsem. High Top was strongly fancied to follow up in the Irish 2000 Guineas but finished unplaced behind Ballymore and returned to Newmarket a sick horse. It was more than two months before he ran again.