The most intriguing subplot in his operation is the relationship with Kilgharrahs Love, a horse he has saddled for 10 races without yet getting that first win together. Ten races is a long run of near-misses, and it speaks to either extraordinary persistence or genuine belief that the breakthrough is coming. Whether that patience is eventually rewarded will say a lot about Cleary's judgment as a trainer.
His most regular jockey is Rory Cleary — likely a family connection — who has ridden 18 times for the yard and come away with 1 winner, a win rate of around 1 in every 18. That is a modest return, but the sheer volume of rides together suggests the partnership is built on trust rather than results alone, which is not unusual for a smaller yard building gradually.
One genuinely encouraging detail: on wet or muddy ground, Cleary's horses have won 1 from 5 races, a win rate of 20%, or 1 in every 5. That outperforms his overall average by some distance and hints that his horses — or his training methods — suit softer conditions particularly well. For a trainer still accumulating experience, finding an edge like that is exactly the kind of pattern worth building on.
| Course | Races | Wins | Win rate |
|---|---|---|---|
| Roscommon | 6 | 0 | 0% |
| Navan | 3 | 2 | 66.7% |
| Dundalk | 3 | 0 | 0% |
| Bellewstown | 2 | 1 | 50% |
| Gowran Park | 2 | 0 | 0% |
| Limerick | 2 | 0 | 0% |
| Down Royal | 1 | 0 | 0% |
| Galway | 1 | 0 | 0% |
| Naas | 1 | 0 | 0% |
| Killarney | 1 | 0 | 0% |
| Fairyhouse | 1 | 0 | 0% |
| Thurles | 1 | 0 | 0% |
| Cork | 1 | 0 | 0% |
| Punchestown | 1 | 0 | 0% |
| The Curragh | 1 | 0 | 0% |