His biggest moment came at Great Yarmouth on 16 September 2021, when he won the Yarmouth, a Class 2 race — which puts it among the better races in Britain. It was also his first career win, and the people around him at the time made no secret of what they thought the result came down to: jockey Adam Kirby followed instructions perfectly on a horse described as "quite a lazy type," with the suggestion that on another day, with another rider, the race might not have gone the same way. That kind of insight into a horse's character is rare and tells you something real — Pleasant Man needs handling, not just riding.
There have been complications along the way. Trainer Joey Ramsden, based in Newark, Nottinghamshire, has spoken about Pleasant Man suffering a bleed when pulled up in a race at Kempton, which led to a breathing operation. It is the sort of setback that can quietly derail a horse's career, and the fact that Pleasant Man has continued to race and place consistently suggests he has come through it reasonably well, even if the wins have been harder to come by since.
On paper, his preferred conditions tell a clear story: he does best over longer distances — between a mile and six furlongs and two miles — and goes well on normal ground, winning 2 of his 9 races in those conditions, which is roughly 1 in every 4.5 races. That is a noticeably better record than his overall figures and suggests he is a horse who rewards patience and the right setup. He raced just yesterday, which confirms he is still active and still being campaigned, even though his last win came at Southwell back in January 2025 — over 16 months ago now. His recent run of form reads 3-7-4-9-2-2, meaning a couple of close finishes are in there. Ramsden's yard has sent out five winners this season. Pleasant Man, given the right day and the right ground, might yet add to that tally.
| Course | Races | Results | Last visited | Win rate |
|---|---|---|---|---|
| Southwell Galloping |
11 | 1 win, 1 second, 1 third, 8 other | 11 Apr | 9.1% |
| Wolverhampton Galloping |
5 | 1 second, 1 third, 3 other | 29 May | 0% |
| Lingfield Park Sharp |
3 | 1 second, 2 other | 19 May | 0% |
| Newcastle Galloping |
3 | 3 other | 5 Dec | 0% |
| Taunton Undulating |
2 | 1 second, 1 third | 7 Feb | 0% |
| Great Yarmouth Galloping |
1 | 1 win | 16 Sep | 100% |
| Fakenham Tight |
1 | 1 win | 2 Jun | 100% |
| chelmsford | 1 | 1 third | 15 Jan | 0% |
| Exeter Undulating |
1 | 1 second | 1 Feb | 0% |
| Newmarket Galloping |
1 | 1 other | 13 Jul | 0% |
| Doncaster Galloping |
1 | 1 other | 2 May | 0% |
| Aintree Galloping |
1 | 1 other | 3 Dec | 0% |
| hereford | 1 | 1 second | 15 Feb | 0% |
| Stratford-on-Avon Sharp |
1 | 1 other | 18 Jun | 0% |
| Kempton Park Galloping |
1 | 1 other | 26 Feb | 0% |
| Musselburgh Sharp |
1 | 1 third | 8 Apr | 0% |
| Ascot Galloping |
1 | 1 other | 20 Jun | 0% |
| Wincanton Galloping |
1 | 1 third | 19 Oct | 0% |