Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| ITF M25 Edmonton | 2023/10/30 16:30 | Junghee You v Henry Lieberman | 1-6,1-6 |
| ITF M25 Saint-Augustin | 2023/10/24 14:00 | Drew Van Orderlain v Henry Lieberman | 6-4,7-6 |
| ITF M25 Saint-Augustin | 2023/10/23 14:00 | Sam Wortzman v Henry Lieberman | 0-6,6-7 |
| UTR Pro Florida | 2023/10/06 18:41 | Benjamin Willwerth v Henry Lieberman | 6-3,1-2 |
| UTR Pro Florida | 2023/10/04 18:00 | Nicolas Jadoun v Henry Lieberman | 6-1,6-4 |
| UTR Pro Florida | 2023/10/03 15:00 | Tristan Bradley v Henry Lieberman | 6-3,6-3 |
| UTR Pro Florida | 2023/10/01 19:15 | Henry Lieberman v John Bernard | 6-4,6-3 |
| Challenger Charleston | 2023/09/24 14:00 | Federico Agustin Gomez v Henry Lieberman | 6-3,6-3 |
| ITF M25 Saint-Augustin | 2023/10/27 16:50 | Mohamed Aziz Dougaz v Clement Chidekh | 7-6,6-3 |
| ITF M25 Saint-Augustin | 2023/10/26 14:55 | Alex Finkelstein v Clement Chidekh | 2-6,2-6 |
| ITF M25 Saint-Augustin | 2023/10/25 14:30 | Mikael Arseneault v Clement Chidekh | 2-6,4-6 |
| Challenger Fairfield | 2023/10/08 21:50 | Clement Chidekh v Colin Markes | 4-6,2-6 |
| Challenger Tiburon | 2023/10/01 19:55 | Brayden Schnur v Clement Chidekh | 6-3,6-2 |
| ITF M25 Setubal | 2023/09/21 12:30 | Clement Chidekh v Jaime Faria | 4-6,5-7 |
| ITF M25 Setubal | 2023/09/19 12:45 | Clement Chidekh v Martim Simoes | 4-6,6-3,6-2 |
| ITF M25 Madrid | 2023/09/15 09:00 | Peter Heller v Clement Chidekh | 6-2,6-3 |