The headline number from the last twelve months is 27 winners from 237 rides, which works out at roughly 1 in every 9 — an 11% win rate. That is a slight dip from last season when he was winning closer to 1 in every 7, and it is worth watching whether that slippage is a blip or the start of a trend. Either way, 166 career winners in four years is a solid foundation for a jockey still in the early stages of a career.
Where Sheppard really stands out is his partnership with trainer Tom Lacey. Across 130 rides together they have produced 25 winners — that is nearly 1 in every 5, or 19%, which is a genuinely strong ratio and suggests a level of trust and communication that goes well beyond simply turning up and doing a job. When a trainer keeps putting you up at that kind of frequency, it usually means you are doing something right in the way you report back, school the horses, and ride to a plan.
He also has a clear preference for racing on normal ground — dry enough to be fast, wet enough to be fair — where he has won 18 from 102 races this season, a rate of roughly 1 in every 6. That is noticeably better than his overall figures, and hints that he — or the horses he rides — can struggle when conditions turn really wet and muddy. Newton Abbot is another bright spot: three winners from just five rides at the track is the kind of record that makes trainers think of you first when they are looking for a jockey there.
Still only four years in, still building. The dip this season is the one thing to keep an eye on — but with big-race experience already banked and a high-performing stable behind him, Sheppard has more than enough to suggest the best is still ahead.
| Course | Races | Wins | Win rate |
|---|---|---|---|
| Chepstow | 24 | 1 | 4.2% |
| Uttoxeter | 19 | 0 | 0% |
| Warwick | 18 | 2 | 11.1% |
| hereford | 17 | 2 | 11.8% |
| Stratford-on-Avon | 12 | 1 | 8.3% |
| Ludlow | 12 | 0 | 0% |
| Worcester | 11 | 1 | 9.1% |
| Market Rasen | 9 | 4 | 44.4% |
| Huntingdon | 8 | 4 | 50% |
| Southwell | 8 | 1 | 12.5% |
| Cheltenham | 8 | 0 | 0% |
| Taunton | 7 | 0 | 0% |
| Bangor-on-Dee | 7 | 0 | 0% |
| Kelso | 6 | 0 | 0% |
| Newton Abbot | 5 | 3 | 60% |
| Ascot | 5 | 1 | 20% |
| Catterick Bridge | 5 | 0 | 0% |
| Exeter | 5 | 0 | 0% |
| Fontwell Park | 4 | 1 | 25% |
| Plumpton | 4 | 1 | 25% |
| Wetherby | 4 | 0 | 0% |
| Wincanton | 4 | 0 | 0% |
| Kempton Park | 4 | 0 | 0% |
| Aintree | 4 | 0 | 0% |
| Ffos Las | 4 | 0 | 0% |
| Haydock Park | 3 | 1 | 33.3% |
| Leicester | 3 | 0 | 0% |
| Newbury | 3 | 0 | 0% |
| Fakenham | 2 | 1 | 50% |
| Ayr | 2 | 1 | 50% |
| Sandown Park | 2 | 1 | 50% |
| Newcastle | 2 | 0 | 0% |
| Lingfield Park | 2 | 0 | 0% |
| Perth | 1 | 1 | 100% |
| Carlisle | 1 | 0 | 0% |
| Cartmel | 1 | 0 | 0% |
| Musselburgh | 1 | 0 | 0% |