Stadium: Court 8 Round: 54 Ground: Hardcourt outdoor
| ITF M15 Winston-Salem | 2023/11/06 17:00 | Raphael Calzi v Henry Lieberman | 2-6,7-5,4-10 |
| ITF M25 Edmonton | 2023/10/31 18:05 | Henry Lieberman v Clement Chidekh | 1-6,7-5,2-6 |
| 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 |
| ITF M25 Harlingen | 2023/10/23 14:00 | Jared Thompkins v Raphael Perot | 2-6,3-6 |
| ITF M15 Morelia | 2023/10/17 18:30 | Juan Sebastian Osorio v Jared Thompkins | 6-3,6-2 |
| ITF M25 Zaragoza | 2023/10/01 11:00 | Samuel Brosset v Jared Thompkins | 6-1,6-0 |
| ITF M25 Sabadell | 2023/09/24 07:30 | Jared Thompkins v Pol Amoros Ramos | 1-6,0-6 |
| ITF M15 Melilla | 2023/09/18 14:00 | Jared Thompkins v Tancredi Alfano | 2-6,4-6 |
| ITF M15 Lakewood | 2023/07/11 17:00 | Jared Thompkins v Wally Thayne | 1-6,1-6 |
| ITF M15 Lakewood | 2023/07/04 17:00 | Jared Thompkins v Alex Jones | 4-6,6-7 |
| ITF M15 Irvine | 2023/06/26 17:00 | Joseph Corse v Jared Thompkins | 6-1,6-3 |