Ground: Hardcourt outdoor
| ITF M15 Vero Beach | 2025/04/25 16:33 | Ryan Dickerson v Keaton Hance | 6-1,6-0 |
| ITF M15 Vero Beach | 2025/04/24 17:00 | Sebastian Gima v Ryan Dickerson | 6-7,6-3,1-6 |
| ITF M15 Vero Beach | 2025/04/23 19:32 | Ryan Dickerson v Drew Van Orderlain | 6-4,5-3 |
| ITF M25 Calabasas | 2025/03/27 17:00 | Ryan Dickerson v Stefan Dostanic | 7-5,3-6,3-6 |
| ITF M25 Calabasas | 2025/03/26 21:47 | Ryan Dickerson v Toby Martin | 6-2,5-3 |
| ITF M25 Calabasas | 2025/03/25 17:00 | Isaiah Strode v Ryan Dickerson | 6-3,7-6 |
| ITF M25 Bakersfield | 2025/03/18 22:00 | Ryan Dickerson v Adam Jones | 4-6,5-7 |
| ITF M15 Tallahassee | 2024/11/19 20:10 | Ryan Dickerson v Jelani Sarr | 6-3,1-6,6-7 |
| Davis Cup | 2025/01/31 14:00 | Oliver Ojakaar v Ignacio Parisca | 6-7,6-4,6-4 |
| ITF M15 Sharm El Sheikh | 2024/11/27 08:00 | Marek Gengel v Oliver Ojakaar | 6-2,3-6,6-1 |
| ITF M15 Sharm El Sheikh | 2024/11/22 08:00 | Alexandr Binda v Oliver Ojakaar | 7-5,6-2 |
| ITF M15 Sharm El Sheikh | 2024/11/21 08:00 | Oliver Ojakaar v Yuta Kawahashi | 6-7,7-6,6-3 |
| ITF M15 Sharm El Sheikh | 2024/11/20 13:25 | Oliver Ojakaar v Ilgiz Kamchibekov | 6-2,6-0 |
| ITF M15 Sharm El Sheikh | 2024/11/19 08:00 | Oliver Ojakaar v Daniil Ostapenkov | 6-2,6-0 |
| ITF M15 Sharm El Sheikh | 2024/11/18 10:30 | Oliver Ojakaar v Vadym Konovchuk | 6-0,6-1 |
| ITF M15 Sharm El Sheikh | 2024/11/17 14:00 | Oliver Ojakaar v Artur Martsinkevich | 6-0,6-2 |