The most telling number in Cleary's record is the partnership with trainer A P O'Brien. From 81 rides together, that combination has produced 14 winners — that's winning roughly 1 in every 6, more than double the rate Cleary achieves overall. When a jockey finds a trainer whose horses suit their style, it can define a whole career, and having that kind of foothold with one of the most respected yards in the sport is a significant asset for someone still in their third year of riding.
Cleary also has a clear preference when the ground gets wet and heavy underfoot. In those muddier conditions, the record reads 7 wins from 35 races — 1 in every 5 — compared to the broader seasonal average of 1 in 13. That's a genuinely striking difference, and it suggests Cleary either rides with particular confidence when conditions get testing, or has simply been placed on horses well-suited to that kind of ground.
Cork is the track where it all tends to come together. Six winners from just 15 rides there means Cleary is winning 2 in every 5 races at that venue — a remarkable hit rate that any jockey at any level of the sport would be proud of. Whether it's familiarity with the track's layout, the type of races run there, or simply that the O'Brien partnership has produced results at Cork specifically, it makes Cleary a name worth watching whenever they're entered there.
Forty-seven career winners in three years won't set the record books alight, but the foundations here are genuinely interesting. A powerful stable relationship, a clear advantage in wet conditions, and one track where confidence clearly runs high — these are the kinds of building blocks that serious careers are made from.
| Course | Races | Wins | Win rate |
|---|---|---|---|
| Dundalk | 56 | 1 | 1.8% |
| The Curragh | 32 | 2 | 6.2% |
| Leopardstown | 24 | 4 | 16.7% |
| Naas | 16 | 3 | 18.8% |
| Cork | 15 | 6 | 40% |
| Gowran Park | 15 | 0 | 0% |
| Navan | 13 | 0 | 0% |
| Galway | 10 | 0 | 0% |
| Listowel | 10 | 0 | 0% |
| Sligo | 9 | 0 | 0% |
| Limerick | 8 | 1 | 12.5% |
| Bellewstown | 8 | 0 | 0% |
| Killarney | 4 | 1 | 25% |
| Tipperary | 4 | 0 | 0% |
| Roscommon | 3 | 0 | 0% |
| Fairyhouse | 3 | 0 | 0% |
| Laytown | 2 | 0 | 0% |
| Ballinrobe | 2 | 0 | 0% |
| Thurles | 1 | 0 | 0% |
| Punchestown | 1 | 0 | 0% |
| Clonmel | 1 | 0 | 0% |
| Down Royal | 1 | 0 | 0% |
| Tramore | 1 | 0 | 0% |