The headline on his CV is five wins at the very top level of the sport — Class 1 races, the kind that matter most. Those have come at venues including Cheltenham, Haydock Park and Ayr, which means he has delivered on the biggest stages, at tracks that draw the biggest crowds and the toughest fields. For a jockey only four years into his career, that is a meaningful achievement. Plenty of riders go entire careers without tasting that level of success.
One partnership stands out. Alongside trainer Barry Connell, Flanagan has won 6 times from 54 rides together — 1 in every 9, which runs ahead of his overall average and suggests the two have developed a real understanding. In racing, a jockey and trainer who click can be greater than the sum of their parts: the trainer knows what the horse needs, and the jockey knows how to deliver it. That relationship looks like one to watch.
There is one note of caution in the data. His win rate has slipped from around 1 in 9 last season to 1 in 13 this year — a dip worth acknowledging, even if it does not tell the whole story. What does stand out, though, is how well he performs on normal ground conditions. On a standard, fair track, Flanagan wins 14 from 83 races — roughly 1 in 6. That is a genuinely eye-catching figure, nearly double his overall average, and it hints at a jockey who is at his very best when conditions are fair and the racing is straightforward. When the ground is neither too wet nor too dry, back Flanagan with more confidence than the raw numbers suggest.
| Course | Races | Wins | Win rate |
|---|---|---|---|
| Fairyhouse | 27 | 3 | 11.1% |
| Limerick | 26 | 3 | 11.5% |
| Galway | 23 | 2 | 8.7% |
| Punchestown | 22 | 2 | 9.1% |
| Wexford | 21 | 3 | 14.3% |
| Tramore | 19 | 1 | 5.3% |
| Navan | 19 | 0 | 0% |
| Listowel | 18 | 1 | 5.6% |
| Cork | 17 | 3 | 17.6% |
| Clonmel | 16 | 0 | 0% |
| Thurles | 15 | 2 | 13.3% |
| Kilbeggan | 14 | 0 | 0% |
| Ballinrobe | 13 | 2 | 15.4% |
| Leopardstown | 13 | 0 | 0% |
| Gowran Park | 12 | 0 | 0% |
| Killarney | 11 | 1 | 9.1% |
| Cheltenham | 11 | 0 | 0% |
| Down Royal | 11 | 0 | 0% |
| Naas | 10 | 1 | 10% |
| Tipperary | 10 | 0 | 0% |
| Downpatrick | 9 | 1 | 11.1% |
| Bellewstown | 7 | 2 | 28.6% |
| Aintree | 3 | 0 | 0% |
| Sligo | 3 | 0 | 0% |
| Roscommon | 2 | 1 | 50% |
| York | 1 | 0 | 0% |