Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Ithaca | 2023/10/03 16:30 | Kaylan Bigun v Matt Kuhar | 3-6,6-4,6-7 |
| ITF M15 Orange Park | 2023/05/03 13:45 | Kaylan Bigun v Huzaifa Abdul Rehman | 6-1,6-7,2-6 |
| ITF M15 Vero Beach | 2023/04/26 19:40 | Gabi Adrian Boitan v Kaylan Bigun | 7-6,6-1 |
| Challenger Tallahassee | 2023/04/17 14:00 | Kaylan Bigun v Ryan Harrison | 2-6,6-7 |
| ITF M15 Sunrise | 2023/04/13 15:00 | Kaylan Bigun v Kyle Kang | 5-7,4-6 |
| ITF M15 Sunrise | 2023/04/11 21:00 | Jesse Flores v Kaylan Bigun | 1-6,4-6 |
| ITF M15 Naples | 2023/02/28 16:30 | Jonathan Mridha v Kaylan Bigun | 6-2,6-0 |
| ITF M15 Antalya | 2022/10/27 07:00 | Kaylan Bigun v Peter Heller | 2-6,2-6 |
| ITF M25 Las Vegas | 2023/10/17 13:00 | Maxwell Exsted v Ryan Dickerson | 4-6,3-6 |
| ITF M25 Las Vegas | 2023/10/16 13:00 | Huzaifa Abdul Rehman v Ryan Dickerson | 3-6,6-1,3-10 |
| ITF M15 Ithaca | 2023/10/04 14:00 | Ryan Dickerson v Gabriel Evans | 2-6,4-6 |
| ITF M15 Albuquerque | 2023/09/28 14:00 | Ryan Dickerson v William Grant | 5-7,1-6 |
| ITF M15 Albuquerque | 2023/09/27 16:25 | Alfredo Perez v Ryan Dickerson | 3-6,3-6 |
| ITF M15 Albuquerque | 2023/09/26 14:00 | Ryan Dickerson v Luca Staeheli | 6-0,6-4 |
| ITF M15 Albuquerque | 2023/09/25 14:00 | Ryan Dickerson v Ryoma Matsushita | 6-1,6-2 |
| ITF M25 Champaign | 2023/09/11 15:00 | Ryan Dickerson v Pierce Rollins | 4-6,1-6 |