The most important relationship in his career so far is with trainer Adrian McGuinness. Of Caffrey's 249 rides for the yard, 21 have ended in the winner's enclosure — a win rate of around 1 in every 12. That kind of sustained partnership doesn't happen by accident. It suggests a jockey who understands how a particular trainer likes horses ridden, who communicates well, and who gets the call when something is expected to run well. Nearly a fifth of all his career winners have come through that one yard.
Where Caffrey really shines is on normal ground conditions. From 131 races on a standard surface, he has won 16 times — roughly 1 in every 8. That 12% win rate is noticeably better than his overall figures and hints at a rider who is at his most fluent and confident when the ground isn't playing tricks. Gowran Park is another place where he has made his mark: 3 winners from just 14 rides at the track is an excellent return, and for a jockey at this stage of his career, having a course where you genuinely perform above the average is a real asset.
The slight dip this season — from 10% to 7% — is worth noting but shouldn't be overstated. Riding 359 races in a year means you're busy, trusted, and in demand. Not every season moves in a straight line upward, and for a jockey still only four years in, the foundation being built here looks solid. The question now is whether he can push his win rate back toward where it was and start converting some of that volume into bigger moments.
| Course | Races | Wins | Win rate |
|---|---|---|---|
| Dundalk | 125 | 15 | 12% |
| The Curragh | 39 | 1 | 2.6% |
| Leopardstown | 25 | 0 | 0% |
| Navan | 21 | 3 | 14.3% |
| Down Royal | 16 | 0 | 0% |
| Galway | 15 | 0 | 0% |
| Gowran Park | 14 | 3 | 21.4% |
| Roscommon | 14 | 1 | 7.1% |
| Naas | 14 | 0 | 0% |
| Cork | 13 | 0 | 0% |
| Bellewstown | 13 | 0 | 0% |
| Ballinrobe | 9 | 0 | 0% |
| Fairyhouse | 8 | 0 | 0% |
| Tipperary | 6 | 0 | 0% |
| Sligo | 4 | 0 | 0% |
| Punchestown | 4 | 0 | 0% |
| Ayr | 4 | 0 | 0% |
| Newcastle | 4 | 0 | 0% |
| Limerick | 3 | 0 | 0% |
| Killarney | 3 | 0 | 0% |
| Laytown | 2 | 1 | 50% |
| Thurles | 1 | 1 | 100% |
| Listowel | 1 | 0 | 0% |
| Clonmel | 1 | 0 | 0% |