Stadium: Court 9 Round: 25 Ground: Hardcourt outdoor
| Challenger Drummondville | 2022/11/14 16:45 | Jaden Weekes v Kai Wehnelt | 2-6,4-6 |
| Challenger Drummondville | 2022/11/13 18:00 | David Poljak v Jaden Weekes | 4-6,6-7 |
| Challenger Calgary | 2022/11/08 21:00 | Jaden Weekes v Skander Mansouri | 2-6,4-6 |
| ITF M25 Saint-Augustin | 2022/10/26 21:30 | Jaden Weekes v Jonathan Sorbo | 5-7,4-6 |
| ITF M15 Ithaca | 2022/10/06 14:00 | Paul Inchauspe v Jaden Weekes | 6-3,6-1 |
| ITF M15 Ithaca | 2022/10/04 23:15 | Jaden Weekes v Kiranpal Pannu | 6-1,6-2 |
| ATP Montreal | 2022/08/06 15:00 | Jaden Weekes v Daniel Altmaier | 3-6,4-6 |
| Challenger Winnipeg | 2022/07/26 00:05 | Liam Broady v Jaden Weekes | 7-5,6-3 |
| ITF M15 Irvine | 2023/06/29 19:45 | Lorenzo Claverie v Gage Brymer | 6-4,6-3 |
| ITF M15 Irvine | 2023/06/28 19:40 | Alexander Kotzen v Gage Brymer | 2-6,4-6 |
| ITF M15 Los Angeles | 2023/06/22 17:55 | Gage Brymer v Arvid Nordquist | 4-6,4-6 |
| ITF M15 Los Angeles | 2023/06/21 22:15 | Gage Brymer v Ethan Schiffman | 6-2,6-2 |
| Challenger Palmas del Mar | 2023/06/11 20:05 | Gage Brymer v Strong Kirchheimer | 4-6,4-6 |
| ITF M15 San Diego | 2023/06/07 15:50 | Mitchell Harper v Gage Brymer | 6-3,7-6 |
| ITF M15 Rancho Santa Fe | 2023/05/31 21:30 | Juan Carlos Aguilar v Gage Brymer | 7-6,6-1 |
| ITF M15 Monastir | 2023/05/23 08:30 | Gage Brymer v Ryuki Matsuda | 2-6,7-6,6-7 |