Formerly a successful amateur jockey, in the sphere of point-to-point racing and under rules, Oliver Greenall spent five years as assistant trainer to legendary North Yorkshire handler Mick Easterby before joining the training ranks in his own right. He launched his business, Oliver Greenall Racing, from his base at Stockton Hall Farm, near Malpas, Cheshire in 2015.
Greenall is a licensed trainer for Flat and National Hunt racing although, to date, his main focus has been on the latter. In that sphere, he enjoyed his most successful season so far in 2020/21, when he saddled 37 winners from 329 runners, at a strike rate of 11%, and amassed just over £303,000 in prize money. Indeed, in April, 2021, he collected his biggest single prize when the 4-year-old Herbiers, ridden by Paddy Brennan, won the bet365 Novices' Championship Final Handicap Hurdle at Sandown Park, worth £38,580 to the winner. By contrast, on the Flat, Greenall is yet to break into double figures in a season. His highest seasonal tally is six winners, which he achieved from 85 runners, at a strike rate of 7%, in 2017.