[1] Aldcroft was apprenticed to Middleham trainer Tom Dawson, and got his big riding opportunity when Thomas Lye, the stable jockey, left his role in contentious circumstances.

The following year, he registered his next Classic win, the 1859 St Leger, for trainer John Scott on Gamester, owned by Sir Charles Monck.

Lord Glasgow took issue with this defeat[2][1] and as a result, Aldcroft lost the ride, with John Wells taking the mount in the St Leger.

Aldcroft and Glasgow had a strange relationship and frequently argued in a manner likened to "lovers' quarrels".

Besides his Classic victories, Aldcroft had won the Goodwood Cup, Queen's Vase, Northumberland Plate and Cesarewitch Handicap amongst other big races.

[1] In his prime, Aldcroft was a "handsome jockey" with "finely chiselled features" and black, bushy side-whiskers.

[1] He married Jane Cartwright, daughter of the jockey who rode Beeswing, and lived with her in Newmarket at Grafton House on the High Street.