Stadium: Court 5 Round: 54 Ground: Hardcourt outdoor
| 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 |
| UTR Pro Tennis Series Texas | 2022/11/17 17:00 | Nini Gabriel Dica v Derrick Chen | 1-6,1-6 |
| ITF M15 Belgrad | 2023/06/25 09:30 | Davud Amirov v Ali Habib | 6-3,6-2 |
| ITF M15 Kuršumlijska Banja | 2023/06/19 10:00 | Piotr Czaczkowski v Ali Habib | 7-5,6-2 |
| ITF M15 Kuršumlijska Banja | 2023/06/18 09:30 | Benjamin Torres v Ali Habib | 3-6,6-2,3-10 |
| ITF M15 Kuršumlijska Banja | 2023/06/15 09:15 | Ali Habib v Kristijan Juhas | 4-6,2-6 |
| ITF M15 Kuršumlijska Banja | 2023/06/13 07:00 | Ali Habib v Novak Novakovic | 4-6,6-3,11-9 |
| ITF M15 Kuršumlijska Banja | 2023/06/12 10:30 | Ali Habib v Benjamin Torres | 1-6,7-6,10-8 |
| ITF M25 Kuršumlijska Banja | 2023/06/06 10:15 | Viktor Jovic v Ali Habib | 4-6,6-2,10-2 |
| ITF M25 Kuršumlijska Banja | 2023/06/05 13:55 | Cahir Warik v Ali Habib | 2-6,6-3,6-10 |