Stadium: Court 5 Round: 19 Ground: Hardcourt outdoor
| Challenger Granby | 2023/07/18 18:05 | James Trotter v Nathan Ponwith | 6-3,7-6 |
| ITF M25 Edwardsville | 2022/07/31 16:00 | Nathan Ponwith v James Trotter | 6-3,4-6,1-6 |
| 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 Cary | 2023/09/11 17:00 | Nathan Ponwith v Garrett Johns | 6-7,2-6 |
| Challenger Cary | 2023/09/10 18:30 | Nathan Ponwith v Ozan Baris | 6-1,6-4 |
| Challenger Stanford | 2023/08/12 18:20 | Gage Brymer v Nathan Ponwith | 1-6,6-1,6-1 |
| Challenger Tiburon | 2023/10/01 21:55 | Trevor Svajda v James Trotter | 6-4,6-1 |
| Challenger Columbus | 2023/09/21 17:45 | James Trotter v Cannon Kingsley | 4-6,7-6,3-6 |
| Challenger Columbus | 2023/09/20 20:10 | Emilio Gomez v James Trotter | 0-6,6-4,3-6 |
| Challenger Columbus | 2023/09/18 16:00 | Elmar Ejupovic v James Trotter | 7-6,3-6,6-7 |
| Challenger Columbus | 2023/09/17 15:30 | Alexander Bernard v James Trotter | 1-6,4-6 |
| Challenger Cary | 2023/09/10 19:55 | Jaimee Floyd Angele v James Trotter | 7-6,7-6 |
| Challenger Winnipeg | 2023/08/13 17:35 | Andrew Fenty v James Trotter | 6-4,2-6,7-6 |
| Challenger Santo Domingo | 2023/08/08 15:10 | James Trotter v Joshua Sheehy | 6-1,3-6,4-6 |