The headline moment came at Aintree on 4 December 2021, when O'Sullivan landed a top-level race — one of the biggest prizes in British racing. For a trainer in his debut year, winning at that level is no small thing. Aintree is one of the most storied venues in the sport, and getting a winner there at a Class 1 meeting early in your career is the kind of result that puts a yard on the map.
Day to day, the partnership with jockey Danny Gilligan is where O'Sullivan's operation looks sharpest. Across 60 rides together, Gilligan has ridden 8 winners — a win rate of around 1 in every 7 and a half races, or 13%. That sits well above the yard's overall average, suggesting O'Sullivan and Gilligan have developed the kind of understanding that makes a real difference when it matters. The trainer also does notably well when conditions turn wet and heavy underfoot — 6 wins from 40 races on muddy ground gives him a 15% win rate in those conditions, meaning he wins roughly 1 in every 7 races when the rain comes. That is a meaningful edge, and worth noting when the forecast looks grim.
There is a slight cloud on the horizon: the win rate has dipped from 11% last season to 8% this time around, which hints that this year has been a little harder going. But the most recent form suggests that may be turning. Over the last two weeks, O'Sullivan has sent out 5 runners and come back with 1 winner — a 20% win rate, more than double his season average. Small sample, but it is the kind of uptick in form that gets people paying attention. The standout partnership with Favori Logique, by contrast, has produced just 1 win from 14 races together — so not every combination clicks. But at 119 career winners and only four years in, the overall trajectory for O'Sullivan is pointing firmly in the right direction.
| Course | Races | Wins | Win rate |
|---|---|---|---|
| Naas | 50 | 1 | 2% |
| Dundalk | 40 | 5 | 12.5% |
| Punchestown | 36 | 1 | 2.8% |
| Fairyhouse | 30 | 2 | 6.7% |
| The Curragh | 21 | 2 | 9.5% |
| Cork | 18 | 1 | 5.6% |
| Gowran Park | 17 | 2 | 11.8% |
| Limerick | 17 | 1 | 5.9% |
| Navan | 16 | 3 | 18.8% |
| Galway | 16 | 3 | 18.8% |
| Wexford | 16 | 1 | 6.2% |
| Leopardstown | 15 | 2 | 13.3% |
| Tipperary | 14 | 1 | 7.1% |
| Roscommon | 13 | 2 | 15.4% |
| Listowel | 13 | 1 | 7.7% |
| Down Royal | 12 | 1 | 8.3% |
| Tramore | 10 | 2 | 20% |
| Thurles | 10 | 1 | 10% |
| Kilbeggan | 9 | 1 | 11.1% |
| Ballinrobe | 9 | 1 | 11.1% |
| Killarney | 8 | 0 | 0% |
| Clonmel | 6 | 0 | 0% |
| Downpatrick | 6 | 0 | 0% |
| Sligo | 6 | 0 | 0% |
| Bellewstown | 4 | 0 | 0% |
| Newcastle | 2 | 0 | 0% |
| Haydock Park | 2 | 0 | 0% |
| Market Rasen | 1 | 0 | 0% |
| Chester | 1 | 0 | 0% |
| Kelso | 1 | 0 | 0% |
| Aintree | 1 | 0 | 0% |