The most interesting pattern in Dempsey's numbers is what happens when conditions turn wet and difficult. On muddy or soft ground, his horses win 4 from every 20 races — a 20% rate that is meaningfully better than his overall figures. That is not a coincidence. It points to a yard that prepares its horses to handle testing conditions, whether through how they are trained, the types of races they are aimed at, or simply a sharp eye for when to run and when to wait.
Then there is Naas. Four winners from just 9 runners at that track is a remarkable return — nearly half the horses he sends there come back with a winner's prize. For context, most trainers would be delighted with 1 in 5 at any racecourse. Dempsey is managing almost 1 in 2. Whether it is that he knows the track well, targets it carefully, or simply that his horses suit its layout, Naas has become something of a happy hunting ground and is well worth watching whenever his runners appear there.
His most productive working relationship is with jockey Keith Donoghue, who has partnered Dempsey's horses to 7 wins from 32 rides — a win rate of roughly 1 in every 4 or 5. That is noticeably better than Dempsey's overall figures, which tells you the two of them are well-matched in how they approach a race. When Donoghue is booked for a Dempsey runner, it is usually worth a second look.
Forty-eight winners in four years is not a headline-grabbing total, but it is the kind of record that experienced observers notice. Dempsey is clearly not throwing horses at races and hoping — he is placing them well, using ground conditions to his advantage, and building partnerships that work. The foundations look solid, and the trajectory points upward.
| Course | Races | Wins | Win rate |
|---|---|---|---|
| Fairyhouse | 19 | 2 | 10.5% |
| Punchestown | 16 | 0 | 0% |
| Leopardstown | 10 | 2 | 20% |
| Naas | 9 | 4 | 44.4% |
| Navan | 9 | 0 | 0% |
| Galway | 8 | 1 | 12.5% |
| Tramore | 7 | 2 | 28.6% |
| Gowran Park | 7 | 1 | 14.3% |
| Bellewstown | 7 | 0 | 0% |
| Downpatrick | 5 | 1 | 20% |
| Down Royal | 4 | 1 | 25% |
| Thurles | 4 | 1 | 25% |
| Cork | 4 | 0 | 0% |
| Wexford | 4 | 0 | 0% |
| Sligo | 3 | 0 | 0% |
| Roscommon | 2 | 0 | 0% |
| Kilbeggan | 2 | 0 | 0% |
| Limerick | 1 | 1 | 100% |
| Ballinrobe | 1 | 0 | 0% |