Stadium: Court 1 Round: 14 Ground: Hardcourt outdoor
| Challenger Champaign | 2023/11/12 19:35 | Nathan Ponwith v Murphy Cassone | 5-7,3-6 |
| Challenger Knoxville | 2023/11/05 19:25 | Alex Rybakov v Nathan Ponwith | 6-4,6-4 |
| ITF M25 Harlingen | 2023/10/25 13:55 | Nathan Ponwith v Marcus McDaniel | 5-7,4-6 |
| ITF M15 Las Vegas | 2023/10/18 16:55 | Nathan Ponwith v Sebastian Dominko | 3-6,6-7 |
| Challenger Fairfield | 2023/10/08 20:05 | Edward Winter v Nathan Ponwith | 6-2,6-2 |
| Challenger Tiburon | 2023/10/01 21:25 | Evan Zhu v Nathan Ponwith | 4-6,6-2,7-6 |
| Challenger Charleston | 2023/09/24 19:50 | Pedro Rodenas v Nathan Ponwith | 6-7,6-1,7-6 |
| Challenger Columbus | 2023/09/17 19:10 | Preston Stearns v Nathan Ponwith | 6-7,6-4,6-3 |
| Challenger Kobe | 2023/11/12 01:00 | James Trotter v Colin Sinclair | 6-4,7-5 |
| Challenger Sydney | 2023/10/30 04:05 | Colin Sinclair v Marc Polmans | 4-6,2-6 |
| Challenger Shenzhen | 2023/10/19 07:55 | Colin Sinclair v Lorenzo Giustino | 3-6,4-6 |
| Challenger Shenzhen | 2023/10/16 07:00 | Evgeny Donskoy v Colin Sinclair | 6-2,3-6,4-6 |
| Challenger Shenzhen | 2023/10/11 03:40 | Thanasi Kokkinakis v Colin Sinclair | 6-2,3-6,6-3 |
| Challenger Shenzhen | 2023/10/10 04:00 | Colin Sinclair v Tsung-Hao Huang | 3-6,6-4,6-2 |
| Challenger Shenzhen | 2023/10/09 09:35 | Colin Sinclair v Ray Ho | 6-3,6-4 |
| ATP Shanghai | 2023/10/02 06:30 | Colin Sinclair v Li Tu | 6-4,4-6,3-6 |