In 1890 he was an emphatic winner of the 2000 Guineas but despite being regarded as a near certainty for the Epsom Derby he finished fourth after spending much of the race attempting to savage other horses and jockeys.

He went on to win a minor race at Royal Ascot and later defeated a strong field to take the valuable Prince of Wales' Stakes at Leicester Racecourse.

[6] In 1888, the English sportsman Sir John Willoughby opened a book on the 1890 Epsom Derby and accepted a bet £100 on Surefoot at odds of 100/1 meaning that he stood to lose £10,000 if the colt won the race.

[11] In the Findon Stakes over six furlongs at Goodwood Racecourse on 2 August Surefoot started at odds of 6/100 against two opponents and won "in a canter" by three lengths from the filly Red Thorn.

[16] Early in 1890 a visitor to Seven Barrows described the colt as "gross in constitution... lusty... clean in the pipes... [with] extraordinary muscular development" and "nearly the finest three-year-old I have ever looked over".

Surefoot had not improved his chances by his "demoniacal temper"[20] and aggressive behaviour as he seemed more intent on attacking other horses than winning the race and at one point Liddiard had great difficulty preventing the colt from biting one of the other jockeys.

[20] Although there was some criticism of Liddiard for not taking the colt to front early in the race, other observers pointed out that Surefoot refused to co-operate with his jockey and blamed the owner and trainer for mollycoddling and "pampering" the horse, thus rendering him temperamentally ill-prepared for the occasion.

He was equipped with blinkers for the Prince of Wales's Stakes over thirteen furlongs and started 5/4 favourite but after leading for most of the way he faded in the straight and finished fourth behind Alloway, Blue Green and Hebrides.

[24] On 9 July the colt was dropped back in distance for the £8,500 Prince of Wales Stakes over one mile at Leicester Racecourse and was made the 5/2 favourite in an eight-runner field which also included Memoir (winner of the Epsom Oaks), Oddfellow (third in the Grand Prix de Paris), Le Nord and Alloway.

The colt began his third campaign in the Great Jubilee Handicap over one mile at Kempton Park Racecourse on 9 May in which he carried top weight of 131pounds and started the 100/30 favourite.

[30] At Royal Ascot he was dropped back to sprint distances for the Queen's Stand Plate and finished down the field behind the two-year-old filly Lady Caroline.