His most consistent working relationship is with trainer Adrian McGuinness, where he has ridden 31 times and won twice — about 1 in every 15 rides together, or 6%. That is not a headline-grabbing number, but steady partnerships like this are the backbone of a jockey's week. McGuinness keeps Cleary in the saddle regularly, and in this game, regular rides are how you improve.
One area where Cleary does show a genuine edge is on wet, muddy ground. In 35 races on soft going he has won 3 times — roughly 1 in every 12, which at 9% is nearly double his overall season average. That is a meaningful difference and suggests he either rides with more confidence when conditions get testing, or that the horses he tends to partner in those conditions suit the slower, heavier surface. Either way, when the forecast is bad, Cleary is worth a closer look.
His association with Apiary, by contrast, has not clicked yet — three races together, no wins. Sometimes the horse and jockey partnership just does not produce the result on paper that everyone hopes for, and three runs is still a small enough sample that it would be unfair to read too much into it.
Cleary is at the stage of his career where consistency and reliability matter more than the big moments. Seventy-seven winners from four years of riding is a real record, built one hard day at a time.
| Course | Races | Wins | Win rate |
|---|---|---|---|
| Dundalk | 118 | 6 | 5.1% |
| The Curragh | 42 | 1 | 2.4% |
| Gowran Park | 22 | 0 | 0% |
| Leopardstown | 21 | 1 | 4.8% |
| Navan | 20 | 1 | 5% |
| Roscommon | 19 | 1 | 5.3% |
| Naas | 19 | 0 | 0% |
| Cork | 17 | 1 | 5.9% |
| Bellewstown | 15 | 1 | 6.7% |
| Galway | 13 | 2 | 15.4% |
| Down Royal | 9 | 1 | 11.1% |
| Limerick | 7 | 0 | 0% |
| Killarney | 6 | 1 | 16.7% |
| Fairyhouse | 6 | 0 | 0% |
| Listowel | 4 | 0 | 0% |
| Sligo | 4 | 0 | 0% |
| Ballinrobe | 3 | 1 | 33.3% |
| Punchestown | 2 | 0 | 0% |
| Tramore | 1 | 0 | 0% |