Estádio: Court 4 Round: 54 Ground: Hardcourt indoor
| ITF - M25 Saint-Augustin | 2023/10/23 14:00 | Drew Van Orderlain v Tom Dynka | 6-0,6-0 |
| ITF - M15 Morelia | 2023/10/18 19:00 | Felix Corwin v Drew Van Orderlain | 6-4,6-2 |
| ITF - M15 Morelia | 2023/10/17 20:55 | Gonzalo Ariel Karakachian v Drew Van Orderlain | 4-6,0-6 |
| ITF - M25 Zapopan | 2023/10/11 15:30 | Drew Van Orderlain v Andres Urrea | 2-6,3-6 |
| ITF - M25 Zapopan | 2023/10/09 17:45 | Drew Van Orderlain v John Horoz Garner | 6-2,6-0 |
| ITF - M25 Zapopan | 2023/10/08 16:00 | Drew Van Orderlain v Bernardo Borges | 6-1,6-0 |
| ITF - M15 Ithaca | 2023/10/03 14:00 | Drew Van Orderlain v Nicaise Muamba | 4-6,6-2,10-12 |
| ITF - M15 Ithaca | 2023/10/02 16:30 | Filip Pieczonka v Drew Van Orderlain | 4-6,6-1,13-15 |
| ITF - M25 Saint-Augustin | 2023/10/23 14:00 | Sam Wortzman v Henry Lieberman | 0-6,6-7 |
| UTR Pro - Flórida | 2023/10/06 18:41 | Benjamin Willwerth v Henry Lieberman | 6-3,1-2 |
| UTR Pro - Flórida | 2023/10/04 18:00 | Nicolas Jadoun v Henry Lieberman | 6-1,6-4 |
| UTR Pro - Flórida | 2023/10/03 15:00 | Tristan Bradley v Henry Lieberman | 6-3,6-3 |
| UTR Pro - Flórida | 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 |