Estadio: Court 3 Round: 25 Ground: Hardcourt outdoor
| ITF M25 Nottingham | 2023/07/15 09:30 | Billy Harris v Toby Samuel | 4-6,4-6 |
| ITF M25 Nottingham | 2023/07/14 10:00 | Toby Samuel v Daniel Cox | 7-5,7-6 |
| ITF M25 Nottingham | 2023/07/13 09:55 | Mats Rosenkranz v Toby Samuel | 3-6,2-6 |
| ITF M25 Nottingham | 2023/07/12 13:55 | Billy Blaydes v Toby Samuel | 2-6,1-6 |
| ITF M25 Nottingham | 2023/07/12 10:30 | Toby Samuel v Luke Saville | 6-1,7-6 |
| Wimbledon | 2023/06/28 10:00 | Sho Shimabukuro v Toby Samuel | 5-7,6-1,6-4 |
| Wimbledon | 2023/06/26 11:45 | Toby Samuel v Antoine Bellier | 6-4,7-6 |
| Challenger de Ilkley | 2023/06/19 17:25 | Toby Samuel v Alex Bolt | 6-2,6-7,5-7 |
| ITF M25 Nottingham | 2023/07/09 15:35 | Derrick Chen v Ali Habib | 1-6,4-6 |
| UTR Pro Calgary | 2023/06/10 17:00 | Derrick Chen v Matthis Ross | 2-6,6-4,3-6 |
| UTR Pro Calgary | 2023/06/09 19:30 | Derrick Chen v John Kim | 7-5,5-2 |
| UTR Pro Calgary | 2023/06/07 20:13 | Derrick Chen v Maxime Mareschal-Hay | 6-2,6-4 |
| UTR Pro Calgary | 2023/06/06 23:03 | Derrick Chen v Junghee You | 5-7,4-6 |
| UTR Pro Calgary | 2023/06/05 21:00 | Emmett Potter v Derrick Chen | 6-7,6-3,3-6 |
| UTR Pro Tennis Series - Texas | 2022/11/20 00:00 | Derrick Chen v Liam Krall | 7-5,3-6,6-3 |
| UTR Pro Tennis Series - Texas | 2022/11/18 23:15 | Sander Jong v Derrick Chen | 6-2,6-0 |