The horse's best work comes over shorter distances — between five and six-and-a-half furlongs — where those 8 career wins have all come. That translates to 8 wins from 25 races at those trips, or nearly 1 in 3, which is a significantly better ratio than the overall record suggests. Dunlop has described Havana Sky as a six-to-seven furlong horse, and the numbers back that up. At Southwell specifically, the record reads 2 wins from just 4 visits — a course where plenty of horses struggle to find their footing but where Havana Sky has clearly taken to the track.
Much of the horse's reputation was forged on the all-weather surfaces during winter. Dunlop revealed during a stable tour in April that Havana Sky won six races in a single year — a remarkable run of form — and was even named horse of the month in December, earning a bonus prize. That kind of recognition does not come easily. The career then hit a speed bump when an injury forced a two-month break after January, which goes some way to explaining the current run of six races without a win. The most recent victory came at Lingfield Park in October 2025, now nine months ago.
Jockey Hector Crouch has been the most regular partner, and the pairing has clicked well: 3 wins from 10 races together gives them a 30% win rate, or 3 in every 10 rides — meaningfully better than the horse's overall average. When Crouch is aboard, something tends to happen.
At five years old and freshly back in work after injury, the interesting question is whether the winter version of Havana Sky — prolific, consistent, and bonus-winning — can be rediscovered. Dunlop sounded genuinely enthusiastic about the return. The people who own this horse clearly love it, and based on recent history, that affection is well earned.
| Course | Races | Results | Last visited | Win rate |
|---|---|---|---|---|
| Wolverhampton Galloping |
11 | 3 wins, 1 second, 2 thirds, 5 other | 6 Jul | 27.3% |
| Lingfield Park Sharp |
8 | 2 wins, 1 second, 5 other | 13 Jul | 25% |
| Southwell Galloping |
4 | 2 wins, 2 other | 28 Feb | 50% |
| Newcastle Galloping |
4 | 4 other | 14 Oct | 0% |
| Kempton Park Galloping |
3 | 2 thirds, 1 other | 15 Sep | 0% |
| Great Yarmouth Galloping |
2 | 2 other | 29 May | 0% |
| chelmsford | 2 | 2 other | 7 Aug | 0% |
| Newmarket Galloping |
2 | 2 other | 19 Jun | 0% |
| Thirsk Galloping |
1 | 1 win | 30 Aug | 100% |
| Doncaster Galloping |
1 | 1 other | 20 Jul | 0% |
| Nottingham Galloping |
1 | 1 other | 18 Jul | 0% |
| Chepstow Galloping |
1 | 1 other | 28 Aug | 0% |