Sir Visto's St Leger was the last of twenty-eight classic wins gained by his trainer Mathew Dawson.

[5] Dawson, who was over seventy at the time had "retired" from large-scale training in 1885, but continued to handle a small number of horses at his Melton House Stable.

He led into the final furlong and held off the late challenge of the filly Float by a short head with the future 1000 Guineas Galeottia in third.

[9] At the end of the year, a writer in The Sportsman noted that Sir Visto had "grown and gone on well", and had been seen working with the stable's 1894 Derby winner Ladas.

[10] Before the season began, Sir Visto was identified as one of the "most-fancied" Derby contenders in what was regarded as an unusually open year, with no dominant champion.

[13] Two weeks later he finished third, beaten a neck and three quarters of a length, to The Owl and Solaro in an "exciting race" for the Newmarket Stakes, with Kirkconnel fourth[14] At Epsom on 29 May, Sir Visto started at odds of 9/1 in a field of fifteen for the Derby.

Sir Visto, ridden by Sam Loates, had been held up at the back of the field and began to make steady "almost unobserved"[16] progress in the last half mile.

A furlong from the finish Sir Visto took the lead and held off the sustained challenge of the outsider Telescope to win an "exciting" and "well contested" race by three-quarters of a length.

[26] He made his seasonal reappearance in the Ascot race on 18 June but although he looked impressive, with one commentator noting that he had "grown into a grand horse",[27] he was never a danger and finished last of the six runners behind Love Wisely.

[28] He did rather better in his next race two weeks later when he finished fifth of the nine runners behind St Frusquin and Persimmon in an exceptionally strong field for the Princess of Wales's Stakes.

Carrying top weight of 142 pounds, he was never able to threaten the winner, but proved too good for the rest of a strong field which included Laveno and Kirkconnel[30] Eleven days later he started 5/4 favourite for the Champion Stakes (a much less valuable race) over the same course and distance, but finished third of the four runners, beaten three quarters of a length and three lengths by Labrador and Marco.