That solitary win came at Kilbeggan on 16 June 2025, and it remains the only time Bossing It has beaten a field outright. A win rate of around 1 in every 15 races is modest by any measure, and the six races since that Kilbeggan success have produced nothing better than a runner-up finish. The most recent form reads 8-5-2 coming into its last run just yesterday, which suggests the horse is at least running consistently without threatening to add to its tally.
The partnership with jockey Sean Flanagan is a curious one. They've teamed up seven times and are yet to win together — 0 from 7 — which is a stat that raises a quiet question about whether this combination has found its ceiling. That said, O'Brien's yard has only sent out one winner this season in total, so Bossing It's struggles aren't happening in isolation. This is a small operation, and results have been hard to come by all round.
What keeps things interesting is that Bossing It is still only six, still racing, and still finishing in the mix often enough to suggest there's a race to be won somewhere down the line. The places keep coming, the Kilbeggan win proves it can get its head in front, and 13 months is a long time to wait for a repeat — but in racing, one good day can change everything.
| Course | Races | Results | Last visited | Win rate |
|---|---|---|---|---|
| Tramore Sharp |
3 | 1 third, 2 other | 20 Apr | 0% |
| Wexford Sharp |
2 | 1 second, 1 other | 3 Jul | 0% |
| Navan Galloping |
2 | 2 other | 14 Dec | 0% |
| Clonmel Sharp |
2 | 2 other | 26 Feb | 0% |
| Kilbeggan Tight |
1 | 1 win | 16 Jun | 100% |
| Listowel Sharp |
1 | 1 other | 1 Jun | 0% |
| Sligo Sharp |
1 | 1 other | 13 Jul | 0% |
| Galway Tight |
1 | 1 third | 8 Sep | 0% |
| Cork Galloping |
1 | 1 other | 17 Jan | 0% |
| Punchestown Galloping |
1 | 1 other | 27 Jan | 0% |