Estadio: Court 9 Round: 25 Ground: Hardcourt indoor
| Challenger de Fairfield | 2023/10/09 20:45 | Patrick Kypson v Aidan Mayo | 6-3,6-7,6-7 |
| Challenger Tiburón | 2023/10/02 22:35 | Alexis Galarneau v Patrick Kypson | 7-6,6-4 |
| Challenger de Charleston | 2023/09/27 16:10 | Patrick Kypson v Ryan Peniston | 2-6,4-6 |
| Challenger de Cary | 2023/09/16 19:00 | Rinky Hijikata v Patrick Kypson | 6-4,6-2 |
| Challenger de Cary | 2023/09/15 23:00 | Patrick Kypson v Tennys Sandgren | 7-6,6-3 |
| Challenger de Cary | 2023/09/14 23:00 | Adam Walton v Patrick Kypson | 5-7,3-6 |
| Challenger de Cary | 2023/09/13 16:00 | Patrick Kypson v Michael Geerts | 6-1,6-3 |
| US Open | 2023/08/24 14:00 | Patrick Kypson v Juncheng Shang | 4-6,6-7 |
| Challenger de Hamburgo | 2023/10/18 08:00 | Javier Barranco Cosano v Gabriel Debru | 6-3,2-6,6-4 |
| Challenger de Hamburgo | 2023/10/16 16:00 | Gabriel Debru v Frederico Ferreira Silva | 6-4,6-1 |
| Challenger de Mouilleron-le-Captif | 2023/10/02 11:00 | Gabriel Debru v Robin Bertrand | 4-6,4-6 |
| Challenger de Mouilleron-le-Captif | 2023/10/01 12:00 | Gabriel Debru v Niklas Schell | 6-4,6-1 |
| Challenger de Orleans | 2023/09/24 10:25 | Gabriel Debru v Tristan Lamasine | 4-6,6-7 |
| Challenger Rennes | 2023/09/13 13:05 | Gabriel Debru v Lucas Poullain | 3-6,3-6 |
| Challenger Rennes | 2023/09/11 12:20 | Gabriel Debru v Gabriel Decamps | 7-5,7-6 |
| Challenger Rennes | 2023/09/10 12:10 | Gabriel Debru v Luca Sanchez | 7-6,6-3 |