Stadium: Stadium Round: 19 Ground: Hardcourt outdoor
| Challenger Winnipeg | 2023/08/13 16:00 | Aidan Mayo v Kelsey Stevenson | 6-4,6-4 |
| Challenger Lexington | 2023/08/04 19:00 | Arthur Cazaux v Aidan Mayo | 6-1,6-4 |
| Challenger Lexington | 2023/08/03 18:20 | Aidan Mayo v Tristan Schoolkate | 3-6,6-4,6-3 |
| Challenger Lexington | 2023/08/01 18:40 | Nathan Ponwith v Aidan Mayo | 4-6,1-6 |
| Challenger Lexington | 2023/07/31 17:10 | Aidan Mayo v Colin Markes | 6-2,7-5 |
| Challenger Lexington | 2023/07/30 17:30 | Aidan Mayo v Cooper Williams | 6-4,6-3 |
| Challenger Salinas | 2023/07/24 16:25 | Altug Celikbilek v Aidan Mayo | 6-4,6-2 |
| ITF M25 Dallas | 2023/07/16 15:50 | Aidan Mayo v Mitchell Krueger | 4-6,0-6 |
| Challenger Winnipeg | 2023/08/13 18:05 | Cleeve Harper v Justin Boulais | 4-6,6-3,6-2 |
| ITF M15 South Bend | 2023/06/21 18:40 | Cleeve Harper v Blaise Bicknell | 3-6,4-6 |
| Challenger Calgary | 2022/11/10 02:15 | Cleeve Harper v Dominik Koepfer | 4-6,1-6 |
| Challenger Calgary | 2022/11/07 22:20 | Cleeve Harper v Max Hans Rehberg | 7-6,3-6,6-4 |
| Challenger Vancouver | 2022/08/14 17:00 | Ulises Blanch v Cleeve Harper | 6-2,7-6 |
| ITF M25 Champaign | 2022/07/20 20:45 | Peter Bertran v Cleeve Harper | 4-6,6-1,6-1 |
| ITF M15 Pittsburgh | 2022/07/13 14:00 | John Bernard v Cleeve Harper | 7-5,7-5 |
| ITF M15 Waco | 2022/07/06 15:20 | Johannus Monday v Cleeve Harper | 6-3,4-6,6-4 |