Stadium: Court 6 Round: 54 Ground: Hardcourt outdoor
| ITF - M15 Boca Raton | 2022/11/16 14:00 | Rowland Phillips v Alex Kuperstein | 6-0,4-6,6-1 |
| ITF M25 - Austin | 2022/11/10 18:30 | Alex Kuperstein v Colin Markes | 0-6,1-6 |
| ITF M25 - Austin | 2022/11/09 16:00 | Tyler Stewart v Alex Kuperstein | 4-6,3-6 |
| ITF - M15 Sharm-el-Sheikh | 2022/10/19 14:10 | Jesse De Jager v Alex Kuperstein | 5-7,3-6 |
| ITF - M15 Sharm-el-Sheikh | 2022/10/18 08:00 | Alex Kuperstein v Riccardo Campagnola | 6-0,6-0 |
| ITF - M15 Sharm-el-Sheikh | 2022/10/17 08:30 | Alex Kuperstein v Christopher Heck | 6-3,6-0 |
| ITF - M15 Sharm-el-Sheikh | 2022/10/12 12:35 | Alex Kuperstein v Ilia Simakin | 4-6,3-6 |
| ITF - M15 Sharm-el-Sheikh | 2022/10/11 08:00 | Alex Kuperstein v Valerio Perruzza | 7-5,7-5 |
| ITF - M15 Boca Raton | 2022/11/14 16:00 | Sean Daryabeigi v Jakub Ostajewski | 6-2,6-3 |
| ITF - M15 Winston-Salem | 2022/11/07 18:00 | James Story v Jakub Ostajewski | 6-2,7-5 |
| ITF M15 Lubbock | 2022/09/21 17:05 | Jakub Ostajewski v Jakub Wojcik | 4-6,4-6 |
| ITF M15 Lubbock | 2022/09/20 14:00 | Wyatt DeMulling v Jakub Ostajewski | 6-1,4-6,4-10 |
| ITF M15 Lubbock | 2022/09/19 16:30 | Zachary Mintz v Jakub Ostajewski | 1-6,0-6 |
| ITF - M15 Champaign | 2022/09/13 15:00 | Alexander Petrov v Jakub Ostajewski | 6-2,6-2 |
| ITF M15 - Überlingen | 2022/08/16 08:00 | Daniel Siniakov v Jakub Ostajewski | 3-6,6-3,10-7 |
| ITF M15 - Waco | 2022/07/06 13:30 | Jakub Ostajewski v Kaylan Bigun | 3-6,3-6 |