The "(5)" beside his name is worth explaining for newcomers — it means he claims a 5lb weight allowance, a perk given to less experienced jockeys to help them compete. Trainers often use claiming jockeys on horses where carrying less weight could make the difference, so it opens doors that might otherwise stay shut.
His most regular partnership is with trainer P J Rothwell, though it has not been a particularly fruitful one — 2 wins from 31 rides together is a thin return, and suggests the combination is still searching for the right horse at the right moment. His overall win rate has also dipped slightly, from 7% last year to 6% this season, which is not a dramatic fall but is the kind of trend a jockey will want to reverse before it becomes a habit.
At 38 career winners over four years, O'Callaghan is a journeyman in the truest sense — working hard, picking up rides where he can, and trying to establish himself in a sport where opportunities at the top level are fiercely competitive. The next year or two will be telling. Claiming allowances do not last forever, and when they go, a jockey has to prove they can win on merit alone.
| Course | Races | Wins | Win rate |
|---|---|---|---|
| Limerick | 16 | 1 | 6.2% |
| Tramore | 12 | 3 | 25% |
| Wexford | 10 | 0 | 0% |
| Punchestown | 9 | 0 | 0% |
| Naas | 8 | 0 | 0% |
| Ballinrobe | 8 | 0 | 0% |
| Galway | 8 | 0 | 0% |
| Killarney | 8 | 0 | 0% |
| Fairyhouse | 7 | 2 | 28.6% |
| Leopardstown | 7 | 0 | 0% |
| Navan | 6 | 1 | 16.7% |
| Cork | 6 | 0 | 0% |
| Thurles | 6 | 0 | 0% |
| Kilbeggan | 5 | 1 | 20% |
| Clonmel | 5 | 0 | 0% |
| Down Royal | 5 | 0 | 0% |
| Gowran Park | 5 | 0 | 0% |
| Sligo | 4 | 0 | 0% |
| Downpatrick | 3 | 0 | 0% |
| Bellewstown | 2 | 0 | 0% |
| Roscommon | 1 | 0 | 0% |
| Laytown | 1 | 0 | 0% |
| Cheltenham | 1 | 0 | 0% |
| The Curragh | 1 | 0 | 0% |
| Tipperary | 1 | 0 | 0% |