The most telling number in Dempsey's record is what happens when Keith Donoghue climbs aboard one of his horses. That combination has clicked in 7 of their 28 races together — a win rate of 25%, or one in every four rides. For context, most trainer-jockey partnerships would be delighted with half that. Something clearly clicks when these two work together, whether that's shared instinct, good communication at home, or simply the right horses being put in front of the right rider.
Dempsey also has a sharp eye for conditions. On genuinely wet, muddy ground — the kind of racing that sorts out the horses who truly love it from those who are just tolerating it — his runners have won 5 from 20, again hitting that 25% mark. That's not luck; that's a trainer who understands his horses well enough to know when the conditions suit them and when to wait for another day.
Then there is Naas. Four winners from just 9 runners at that track is a remarkable ratio — nearly 1 in every 2 runners making it to the winner's enclosure. Racecourses have their own rhythms and quirks, and trainers who figure out which tracks suit their horses tend to come back there often. Dempsey has clearly cracked the code at Naas, and it would be no surprise to see him keep targeting it.
Still only four seasons in, the overall numbers are modest in size but strong in quality. Forty-seven winners is a decent foundation, and the win rate of 14% across the last year suggests a trainer who picks his spots carefully rather than running horses for the sake of it. The ingredients — a reliable jockey partnership, a feel for heavy ground, and a happy hunting ground at Naas — point to someone building something deliberately and patiently. Worth watching closely.
| Course | Races | Wins | Win rate |
|---|---|---|---|
| Fairyhouse | 19 | 3 | 15.8% |
| Punchestown | 14 | 0 | 0% |
| Leopardstown | 10 | 2 | 20% |
| Naas | 9 | 4 | 44.4% |
| Tramore | 9 | 2 | 22.2% |
| Navan | 9 | 0 | 0% |
| Galway | 8 | 1 | 12.5% |
| Gowran Park | 6 | 0 | 0% |
| Downpatrick | 5 | 1 | 20% |
| Thurles | 4 | 1 | 25% |
| Down Royal | 4 | 1 | 25% |
| Bellewstown | 4 | 0 | 0% |
| Cork | 4 | 0 | 0% |
| Wexford | 3 | 0 | 0% |
| Sligo | 3 | 0 | 0% |
| Roscommon | 2 | 0 | 0% |
| Ballinrobe | 2 | 0 | 0% |
| Limerick | 1 | 1 | 100% |
| Kilbeggan | 1 | 0 | 0% |