Stadium: Brenda Meyers Court Round: 28 Ground: Hardcourt indoor
| Challenger Charlottesville | 2023/11/03 17:20 | Beibit Zhukayev v Nino Serdarusic | 6-3,6-4 |
| Challenger Charlottesville | 2023/11/02 18:30 | Inaki Montes-De La Torre v Beibit Zhukayev | 4-6,6-7 |
| Challenger Charlottesville | 2023/10/30 21:10 | Thai-Son Kwiatkowski v Beibit Zhukayev | 6-4,6-7,6-7 |
| Challenger Shenzhen | 2023/10/18 02:00 | Beibit Zhukayev v Aleksandar Kovacevic | 4-6,7-6,0-6 |
| Challenger Shenzhen | 2023/10/17 02:00 | Beibit Zhukayev v Xiaofei Wang | 6-3,6-4 |
| Challenger Shenzhen | 2023/10/13 03:00 | Beibit Zhukayev v Egor Gerasimov | 7-6,2-6,3-6 |
| Challenger Shenzhen | 2023/10/12 02:00 | Thanasi Kokkinakis v Beibit Zhukayev | 3-6,4-6 |
| Challenger Shenzhen | 2023/10/11 05:45 | Beibit Zhukayev v Zhe Li | 6-4,6-4 |
| Challenger Charlottesville | 2023/11/03 16:00 | Patrick Kypson v Brandon Holt | 6-1,6-4 |
| Challenger Charlottesville | 2023/11/01 18:20 | Denis Kudla v Patrick Kypson | 1-6,3-6 |
| Challenger Charlottesville | 2023/10/30 19:30 | Patrick Kypson v Gabriel Debru | 6-4,7-5 |
| Challenger Fairfield | 2023/10/09 20:45 | Patrick Kypson v Aidan Mayo | 6-3,6-7,6-7 |
| Challenger Tiburon | 2023/10/02 22:35 | Alexis Galarneau v Patrick Kypson | 7-6,6-4 |
| Challenger Charleston | 2023/09/27 16:10 | Patrick Kypson v Ryan Peniston | 2-6,4-6 |
| Challenger Cary | 2023/09/16 19:00 | Rinky Hijikata v Patrick Kypson | 6-4,6-2 |
| Challenger Cary | 2023/09/15 23:00 | Patrick Kypson v Tennys Sandgren | 7-6,6-3 |