| UTR Pro Tuscaloosa | 11/15 15:00 | 53 | Jacob Olar v Lachlan Brain | Walkover | |
| UTR Pro Tuscaloosa | 11/13 22:35 | 28 | Jacob Olar v Brendan Loh | Retired | |
| UTR Pro Tuscaloosa | 11/12 20:00 | - | Jacob Olar v Izan O G Retamero | 6-2,3-6,6-7 | |
| UTR Pro Tuscaloosa | 11/11 23:05 | - | Jacob Olar v Vit Kalina | 2-6,2-6 | |
| UTR Pro Tuscaloosa | 11/10 21:40 | - | Jacob Olar v Joseph Nau | 6-7,6-4,6-4 | |
| ITF M25 Grasse | 06/15 07:30 | 25 |
Matthew Dellavedova
v
Jacob Olar |
6-1,6-0 | |
| ITF M15 Lubbock | 09/19 14:00 | 54 | Pranav Kumar v Jacob Olar | 4-6,6-1,10-6 | |
| ITF M15 Cancun | 08/07 15:30 | 44 | Jacob Olar v Diego Lopato-Miguel | Retired |