The most telling number in Winn's record is the one attached to his partnership with trainer David O'Meara. Seventeen wins from 140 races together gives them a win rate of around 1 in 8 — noticeably better than Winn's overall average — which tells you this is a working relationship built on genuine trust. When a trainer keeps putting you up on their horses at that volume, it means they like what they see. O'Meara runs a major northern yard with serious string depth, so a jockey who consistently delivers for him is in a good place to grow.
Winn also has a knack for riding well when the ground gets a little soft underfoot. On wet or testing ground he has won 4 of 26 races — around 1 in every 6 — which is a meaningfully better return than his overall figures suggest. That kind of adaptability matters in Britain, where the weather rarely cooperates, and jockeys who can handle a horse confidently in trickier conditions tend to attract more calls on rainy days when others might be avoided.
Carlisle is worth flagging too. Three winners from just 11 races at the track gives him a win rate of better than 1 in 4 there — the sort of local dominance that gets noticed by trainers looking to place horses at a specific venue. Tracks have personalities, and jockeys who learn them well — the cambers, the gradients, where to save ground and where to commit — earn a real edge.
At 131 career winners and still only four years in, Winn is on a trajectory that rewards watching. He is not yet a headline name, but the foundations — a productive stable partnership, a feel for testing ground, and a course or two where he clearly thrives — are exactly what a young jockey needs to keep climbing.
| Course | Races | Wins | Win rate |
|---|---|---|---|
| Newcastle | 84 | 9 | 10.7% |
| Southwell | 31 | 3 | 9.7% |
| Doncaster | 29 | 2 | 6.9% |
| Wolverhampton | 29 | 1 | 3.4% |
| Thirsk | 25 | 1 | 4% |
| Beverley | 18 | 0 | 0% |
| Redcar | 16 | 4 | 25% |
| Ripon | 15 | 1 | 6.7% |
| Catterick Bridge | 12 | 1 | 8.3% |
| York | 12 | 0 | 0% |
| Carlisle | 11 | 3 | 27.3% |
| Ayr | 11 | 0 | 0% |
| Nottingham | 10 | 2 | 20% |
| Hamilton Park | 9 | 2 | 22.2% |
| Leicester | 7 | 1 | 14.3% |
| Musselburgh | 5 | 0 | 0% |
| Haydock Park | 5 | 0 | 0% |
| Ascot | 4 | 0 | 0% |
| Pontefract | 3 | 1 | 33.3% |
| Chester | 2 | 0 | 0% |
| Goodwood | 1 | 1 | 100% |
| chelmsford | 1 | 0 | 0% |
| Newmarket | 1 | 0 | 0% |
| Kempton Park | 1 | 0 | 0% |