His overall numbers tell an interesting story. Since turning professional in 2021, Flanagan has ridden 151 winners — a solid foundation for someone still in the early chapters of their career. This season has been busier than ever, with 369 rides, but the win rate has slipped slightly: 31 winners, roughly 1 in every 12 races, compared to around 1 in every 9 last year. That dip is worth watching, but it is not alarming. More rides often means more work for smaller yards on tricky horses, and the sheer volume of racing he is getting through speaks to a jockey whose phone is ringing regularly.
Where Flanagan really catches the eye is on normal ground — when conditions are neither too wet nor too dry, just a standard racing surface. In those conditions he has won 15 from 86 races, a rate of 17%, or roughly 1 in every 6. That is more than double his overall season average, and it suggests a rider who finds his best rhythm when the ground does not complicate matters. Keep an eye on the forecast.
His strongest professional relationship is with trainer Barry Connell, with whom he has built a record of 6 wins from 55 rides together — winning roughly 1 in every 9, which edges ahead of his season average. That kind of consistent partnership matters in racing: a jockey who understands a trainer's horses, and a trainer who trusts a jockey with their best chances, is a combination that tends to produce results when it counts.
Most recently, Flanagan landed a top-level win at Ayr on 12 April 2025, a reminder that even in a season where his overall numbers have softened a little, the quality is still very much there. He is a jockey building something real — not just a career measured in numbers, but a reputation built on big-day performances at the sport's most respected venues.
| Course | Races | Wins | Win rate |
|---|---|---|---|
| Fairyhouse | 34 | 4 | 11.8% |
| Limerick | 28 | 4 | 14.3% |
| Wexford | 26 | 4 | 15.4% |
| Galway | 23 | 2 | 8.7% |
| Tramore | 22 | 1 | 4.5% |
| Punchestown | 21 | 2 | 9.5% |
| Navan | 19 | 0 | 0% |
| Listowel | 18 | 1 | 5.6% |
| Cork | 17 | 3 | 17.6% |
| Naas | 16 | 1 | 6.2% |
| Ballinrobe | 15 | 2 | 13.3% |
| Thurles | 15 | 2 | 13.3% |
| Clonmel | 14 | 0 | 0% |
| Leopardstown | 13 | 0 | 0% |
| Kilbeggan | 12 | 0 | 0% |
| Cheltenham | 12 | 0 | 0% |
| Gowran Park | 12 | 0 | 0% |
| Killarney | 11 | 1 | 9.1% |
| Tipperary | 10 | 0 | 0% |
| Downpatrick | 9 | 1 | 11.1% |
| Down Royal | 9 | 0 | 0% |
| Bellewstown | 4 | 1 | 25% |
| Sligo | 3 | 0 | 0% |
| Ayr | 2 | 1 | 50% |
| Roscommon | 2 | 1 | 50% |
| York | 1 | 0 | 0% |
| Aintree | 1 | 0 | 0% |