| UTR Pro Florida | 2023/10/05 14:00 | Benjamin Willwerth v Paul Spencer | 6-4,6-2 |
| 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 Jablonec Nad Nisou | 2023/08/29 10:30 | Vojtech Mares v Henry Lieberman | 6-7,6-4,10-5 |
| ITF M25 Jablonec Nad Nisou | 2023/08/28 09:00 | Henry Lieberman v Jiri Jindacek | 7-5,6-1 |
| ITF M25 Jablonec Nad Nisou | 2023/08/27 09:00 | Jiri Krouzek v Henry Lieberman | 1-6,2-6 |
| ITF M15 Huy | 2023/08/21 14:35 | Petro Orlando Fellin v Henry Lieberman | 6-1,6-3 |