The most puzzling number in Leonard's recent record is his partnership with trainer Diego Dias — 18 rides together and not a single winner between them. That kind of run is worth noting because 18 attempts is a meaningful sample. Whatever the reasons, it has not clicked yet, and that blank alongside his overall numbers explains why this has been a difficult season to get momentum going.
There is, however, one small but genuine bright spot. On slightly wet ground, Leonard wins 1 in every 14 races — 7% compared to his overall 4% this season. That might sound like a minor difference, but in percentage terms it is nearly double his usual rate. It hints that when conditions suit, he is capable of raising his game, and it is the kind of edge that patient yards may start to factor in when the forecast turns grey.
At 20 career winners and four years in, Leonard is at a crossroads that many young jockeys will recognise — experienced enough to know what is required, but still waiting for the run of form or the right horse that shifts perceptions. The numbers are not yet where he would want them, but the foundation is there.
| Course | Races | Wins | Win rate |
|---|---|---|---|
| Dundalk | 57 | 1 | 1.8% |
| The Curragh | 16 | 0 | 0% |
| Cork | 11 | 1 | 9.1% |
| Gowran Park | 11 | 0 | 0% |
| Naas | 9 | 0 | 0% |
| Killarney | 7 | 1 | 14.3% |
| Fairyhouse | 6 | 0 | 0% |
| Navan | 6 | 0 | 0% |
| Tipperary | 4 | 2 | 50% |
| Bellewstown | 4 | 0 | 0% |
| Limerick | 4 | 0 | 0% |
| Leopardstown | 4 | 0 | 0% |
| Listowel | 3 | 0 | 0% |
| Tramore | 3 | 0 | 0% |
| Thurles | 2 | 1 | 50% |
| Ballinrobe | 2 | 0 | 0% |
| Punchestown | 2 | 0 | 0% |
| Galway | 1 | 0 | 0% |
| Roscommon | 1 | 0 | 0% |
| Down Royal | 1 | 0 | 0% |
| Clonmel | 1 | 0 | 0% |