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 Monastir | 2023/04/18 08:30 | Adrien Gobat v Gage Brymer | 6-0,6-1 |
| ITF M15 Monastir | 2023/04/13 10:35 | Sebastian Sorger v Gage Brymer | 6-2,6-2 |
| ITF M15 Monastir | 2023/04/12 09:45 | Lukas Palovic v Gage Brymer | 3-6,3-6 |
| ITF M25 Calabasas | 2023/03/23 19:40 | Kris Van Wyk v Gage Brymer | 7-6,6-4 |
| ITF M25 Bakersfield | 2023/03/16 19:00 | Alex Bolt v Gage Brymer | 6-3,6-4 |
| ITF M25 Bakersfield | 2023/03/15 23:50 | Gage Brymer v Blu Baker | 7-6,6-4 |
| Challenger Rome GA | 2023/02/19 19:35 | Coleman Wong v Gage Brymer | 4-6,6-3,6-0 |
| Challenger Cleveland | 2023/01/29 16:05 | Gage Brymer v Toby Alex Kodat | 4-6,2-6 |