| UTR Pro Easton | 2023/04/03 12:30 | Luke Simkiss v Stefan Cooper | 6-7,5-7 |
| UTR Pro London | 2023/05/17 07:00 | Luke Simkiss v Ivan Denisov | 2-6,7-5,6-4 |
| UTR Pro London | 2023/05/16 08:30 | Luke Simkiss v Victor Sklenka | 6-7,7-6,7-6 |
| UTR Pro London | 2023/05/15 10:00 | Franco Capalbo v Luke Simkiss | 4-6,0-6 |
| ITF M25 Nottingham | 2023/04/26 11:55 | Giles Hussey v Luke Simkiss | 6-4,6-3 |
| ITF M25 Nottingham | 2023/04/25 09:00 | Yujiro Onuma v Luke Simkiss | 3-6,4-6 |
| ITF M25 Nottingham Qual | 2023/04/24 12:05 | Luke Simkiss v Jimmy Yang | 6-4,7-6 |
| ITF M25 Nottingham | 2023/04/17 10:50 | Luke Simkiss v Alexis Canter | 6-4,6-7,9-11 |
| ITF M25 Nottingham | 2023/04/16 10:40 | Adam Jones v Luke Simkiss | 5-7,3-6 |
| UTR Pro London | 2023/05/18 07:00 | Victor Sklenka v Stefan Cooper | 3-6,6-1,5-6 |
| UTR Pro London | 2023/05/16 07:00 | Franco Capalbo v Stefan Cooper | 4-6,6-1,6-4 |
| UTR Pro London | 2023/05/15 10:00 | Stefan Cooper v Ivan Denisov | 2-6,4-6 |
| UTR Pro Easton | 2023/04/07 11:30 | Stefan Cooper v Kyle Rae | 6-7,6-6 |
| UTR Pro Easton | 2023/04/06 07:00 | Marshall Tutu v Stefan Cooper | 3-6,7-5,6-3 |
| UTR Pro Easton | 2023/04/05 11:30 | Ching Wah Wai v Stefan Cooper | 7-5,7-5 |
| UTR Pro Easton | 2023/04/03 12:30 | Luke Simkiss v Stefan Cooper | 6-7,5-7 |
| UTR Pro Easton | 2023/04/02 07:00 | Stefan Cooper v Richard Bloomfield | 6-2,4-6,4-6 |