Stadium: Court 5 Round: 54 Ground: Clay
| ITF M15 Boca Raton | 2023/11/17 18:00 | Matthew Segura v Arvid Nordquist | 4-6,3-6 |
| ITF M15 Boca Raton | 2023/11/17 14:00 | Matthew Segura v Martin Katz | 7-5,7-5 |
| ITF M15 Tallahassee | 2023/10/25 18:30 | Felix Corwin v Matthew Segura | 6-2,6-4 |
| UTR Pro Atlanta | 2023/06/13 17:10 | Matthew Segura v Corey Craig | 3-6,1-6 |
| UTR Pro Atlanta | 2023/06/12 21:52 | Matthew Segura v Michael Ross | 4-6,4-6 |
| UTR Pro Florida | 2023/05/28 16:33 | Jamie Connel v Matthew Segura | 4-6,7-6,6-0 |
| UTR Pro Florida | 2023/05/27 18:30 | Isaac Nortey v Matthew Segura | 5-7,4-6 |
| UTR Pro Florida | 2023/05/26 19:50 | Matthew Segura v Noureldin Adam | 6-0,3-6,6-3 |
| ITF M15 Tallahassee | 2023/10/25 14:00 | Karl Poling v Ryan Dickerson | 6-7,6-1,6-2 |
| ITF M15 Las Vegas | 2023/10/19 20:50 | Ryan Dickerson v Thai-Son Kwiatkowski | 2-6,3-6 |
| ITF M15 Las Vegas | 2023/10/18 22:30 | Kaylan Bigun v Ryan Dickerson | 6-7,7-6,3-6 |
| 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 |