The turning point in his career came in September 2021, when he scored his first win at Great Yarmouth in a Class 2 race — a top-level success that proved he belonged at the highest level. Since then, his record has been patchy, but trainer Joey Ramsden, who operates from Newark in Nottinghamshire, has clearly found something that works. The secret, it seems, is normal ground conditions. Pleasant Man thrives on a standard track, winning three races out of ten on such surfaces — a 30% win rate that is nearly three times better than his overall record. When the ground turns soft and muddy or becomes unusually firm and fast, his performances dip noticeably.
What makes Pleasant Man interesting is less about raw ability and more about temperament and timing. Ramsden once observed that Pleasant Man is "quite lazy" — not the kind of horse that will drag itself to victory without help. That matters, because a jockey must understand him fully. Adam Kirby, who rode him to success at Yarmouth, was praised for giving him exactly the ride he needed, the kind of handling that another jockey might have missed. For a horse that wins once every eight races, that margin between the right pilot and the wrong one could be the difference between victory and defeat. At eight years old and still actively racing, Pleasant Man may not be a star, but he remains capable of rewarding patient hands with another win when conditions suit him.
| Course | Races | Results | Last run | Win rate |
|---|---|---|---|---|
| Southwell Galloping |
11 | 1 win, 1 second, 1 third, 8 other | 11 Apr | 9.1% |
| Wolverhampton Galloping |
6 | 1 second, 2 thirds, 3 other | 16 Jun | 0% |
| Lingfield Park Sharp |
3 | 1 second, 2 other | 19 May | 0% |
| Newcastle Galloping |
3 | 3 other | 5 Dec | 0% |
| Doncaster Galloping |
2 | 1 win, 1 other | 20 Jun | 50% |
| Great Yarmouth Galloping |
2 | 1 win, 1 third | 2 Jul | 50% |
| Taunton Undulating |
2 | 1 second, 1 third | 7 Feb | 0% |
| Fakenham Tight |
1 | 1 win | 2 Jun | 100% |
| Nottingham Galloping |
1 | 1 win | 1 Oct | 100% |
| Ascot Galloping |
1 | 1 other | 20 Jun | 0% |
| Musselburgh Sharp |
1 | 1 third | 8 Apr | 0% |
| Exeter Undulating |
1 | 1 second | 1 Feb | 0% |
| hereford | 1 | 1 second | 15 Feb | 0% |
| Aintree Galloping |
1 | 1 other | 3 Dec | 0% |
| Kempton Park Galloping |
1 | 1 other | 26 Feb | 0% |
| Newmarket Galloping |
1 | 1 other | 13 Jul | 0% |
| chelmsford | 1 | 1 third | 15 Jan | 0% |
| Wincanton Galloping |
1 | 1 third | 19 Oct | 0% |
| Haydock Park Galloping |
1 | 1 other | 25 Sep | 0% |
| York Galloping |
1 | 1 other | 10 Jul | 0% |
| Stratford-on-Avon Sharp |
1 | 1 other | 18 Jun | 0% |