Stadium: Center Court Round: 14 Ground: Hardcourt outdoor
| Challenger Columbus | 2023/09/20 18:50 | Enzo Couacaud v Federico Agustin Gomez | 7-5,6-4 |
| Challenger Columbus | 2023/09/19 16:00 | Federico Agustin Gomez v Ethan Quinn | 7-5,7-6 |
| Challenger Columbus | 2023/09/18 17:55 | Federico Agustin Gomez v Robert Cash | 6-4,6-3 |
| Challenger Columbus | 2023/09/17 14:00 | Federico Agustin Gomez v Brayden Schnur | 7-6,7-6 |
| Challenger Cary | 2023/09/10 15:00 | Federico Agustin Gomez v Donald Young | 3-6,6-3,2-6 |
| Challenger Praga | 2023/08/24 09:00 | Federico Agustin Gomez v Rudolf Molleker | 3-6,3-6 |
| Challenger Praga | 2023/08/23 09:45 | Federico Agustin Gomez v Lorenzo Giustino | 6-3,6-3 |
| Challenger Praga | 2023/08/22 09:50 | Henri Squire v Federico Agustin Gomez | 6-4,4-6,3-6 |
| ITF - Jablonec Nad Nisou M25 | 2023/08/29 10:30 | Vojtech Mares v Henry Lieberman | 6-7,6-4,10-5 |
| ITF - Jablonec Nad Nisou M25 | 2023/08/28 09:00 | Henry Lieberman v Jiri Jindacek | 7-5,6-1 |
| ITF - Jablonec Nad Nisou M25 | 2023/08/27 09:00 | Jiri Krouzek v Henry Lieberman | 1-6,2-6 |
| ITF - Huy M15 | 2023/08/21 14:35 | Petro Orlando Fellin v Henry Lieberman | 6-1,6-3 |
| ITF - Huy M15 | 2023/08/21 08:40 | Henry Lieberman v Maxime Dubouch | 6-3,6-3 |
| ITF - Huy M15 | 2023/08/20 13:30 | Henry Lieberman v Benoit Torcq | 3-6,6-3,10-8 |
| ITF - Kottingbrunn M15 | 2023/08/13 12:00 | Jiri Jindacek v Henry Lieberman | 6-4,6-4 |
| UTR Pro Tennis Series - Floryda | 2022/12/14 19:00 | Aleksandar Mitric v Henry Lieberman | 6-3,3-6,5-4 |