Like his sire, Captain Cuttle was trained throughout his career by Fred Darling at Beckhampton in Wiltshire,[3] and was ridden in his most important races by the leading British jockey of the era Steve Donoghue.

Captain Cuttle's heavy physique and immaturity put a strain on his forelegs, leading Darling to treat him very carefully, riding the colt himself in most of his exercise work.

[6] Captain Cuttle began his three-year-old season in the Wood Ditton Stakes at Newmarket Racecourse, which he won by six lengths.

Allegations were later made in the Daily Express that Captain Cuttle had been illegally injected with cocaine, to combat lameness caused by the incident.

[9] The colt was reported to be lame after the race and there were rumours that his career was over[10] but he appeared to have recovered in time for Royal Ascot where he won the St James's Palace Stakes over a mile.

He had some success, siring the 1000 Guineas winner Scuttle but did not live up to expectations and was sold for a reported £40,000 to stand in Italy in 1927.