Stadium: Court 7 Round: 62 Ground: Clay
| Challenger Drummondville | 2023/11/12 22:55 | Kelsey Stevenson v Patrick Brady | 6-7,4-6 |
| Challenger Calgary | 2023/11/05 17:00 | Kelsey Stevenson v Patrick Brady | 2-6,1-6 |
| Challenger Winnipeg | 2023/08/13 16:00 | Aidan Mayo v Kelsey Stevenson | 6-4,6-4 |
| Challenger Medellin | 2023/06/26 18:00 | Tristan McCormick v Kelsey Stevenson | 6-4,7-6 |
| ITF M25 Jakarta | 2023/04/17 07:55 | Blake Bayldon v Kelsey Stevenson | 6-7,1-6 |
| ITF M25 Jakarta | 2023/04/10 06:05 | Corban Crowther v Kelsey Stevenson | 7-5,6-3 |
| ITF M15 Singapore | 2023/04/05 05:25 | Kelsey Stevenson v Seon Yong Han | 6-2,4-6,2-6 |
| ITF M25 Lucknow | 2023/03/20 04:30 | Kelsey Stevenson v Yash Chaurasia | 1-6,6-7 |