The headline moment came on 16 April 2025 at Cheltenham, where he won a top-level Class 2 race — one of the better prizes in British racing. That completed a three-win season that began with a sharp victory at Ascot in December, where his jockey Freddie Gordon noticed the horse was jumping so well he rang Henderson before the next race to suggest a quick turnaround at Kempton Park just six days later. Henderson left Gordon on, partly so the young jockey could use a weight allowance that would help the horse's chances. It worked. East India Express won again, and the confidence that built through the winter carried him all the way to Cheltenham.
The Kempton connection is worth underlining. East India Express has raced there three times and won all three. A 100% record at any track is rare, and at a venue like Kempton it speaks to a horse that genuinely suits quick, flat, fair racing on normal ground — he has won 4 of his 6 races when conditions are standard, a 67% win rate that is simply extraordinary for a sport where even the best horses lose more than they win.
Freddie Gordon has been the constant through much of this. The pair have won 3 of their 9 races together — 1 in every 3 — and the post-race quotes from Cheltenham made clear how much of a partnership this has become, with Henderson crediting Gordon warmly even after champion jockey Nico de Boinville came in for the festival win.
The big question now is what comes next. Henderson has said publicly he is weighing up whether East India Express stays over hurdles or tries jumping fences — a different and more demanding discipline. Gordon's observation after Ascot, that the horse might actually respect a fence more than a hurdle, hints there could be something to discover. The last six races have produced no wins, but one of those was a Cheltenham Class 2 victory. This horse is very much still in the conversation.
| Course | Races | Results | Last visited | Win rate |
|---|---|---|---|---|
| Cheltenham Galloping |
4 | 1 win, 3 other | 13 Mar | 25% |
| Newbury Galloping |
4 | 1 second, 3 other | 29 Nov | 0% |
| Kempton Park Galloping |
3 | 3 wins | 26 Dec | 100% |
| Ascot Galloping |
1 | 1 win | 20 Dec | 100% |
| Windsor Sharp |
1 | 1 second | 1 Jan | 0% |
| Leicester Sharp |
1 | 1 other | 13 Dec | 0% |
| Punchestown Galloping |
1 | 1 other | 1 May | 0% |
| Plumpton Sharp |
1 | 1 other | 19 Apr | 0% |