That sole win came at Haydock Park on 30 December 2025, and it clearly meant something to the yard. Oliver Greenall and Josh Guerriero, who train out of Oldcastle in Cheshire, have been bullish about Diamond Jim ever since. Speaking earlier this year, they described him as a "tough little horse" who has done well this season — and with 43 winners already on the board this season, this is a team that knows what a good horse looks like. When they say he's done well, it's worth listening. At the level Diamond Jim typically competes — Class 4, which is solid mid-tier racing — he's won 1 from 3, a 33% win rate at that grade, or roughly 1 in every 3 races. That's a promising return.
What makes Diamond Jim genuinely interesting is what comes next. The Greenall and Guerriero team have earmarked him to jump fences next season, which is a significant step up in challenge and excitement. Right now he races over hurdles — smaller obstacles — but fences are the bigger, more dramatic test, the kind of racing most people picture when they think of jump racing. The fact that his trainers are pointing him in that direction suggests they believe he has the scope and the jumping ability to handle it. He's been racing as recently as yesterday, so there's clearly no sign of anything slowing him down between now and the end of the season.
His recent form — a mix of a win, a couple of placed efforts, and some quieter runs — paints the picture of a horse still finding his feet and improving as he matures. Four is young in this game. The best is potentially still ahead.
| Course | Races | Results | Last visited | Win rate |
|---|---|---|---|---|
| Bangor-on-Dee Sharp |
2 | 1 second, 1 other | 18 Apr | 0% |
| Haydock Park Galloping |
1 | 1 win | 30 Dec | 100% |
| Aintree Galloping |
1 | 1 other | 6 Dec | 0% |
| Warwick Sharp |
1 | 1 other | 23 Jan | 0% |
| Sedgefield Sharp |
1 | 1 other | 1 Apr | 0% |