| UTR Pro Newport Beach | 01/08 18:45 | - | Gabriel Jessup v Parashar Bharadwaj | CANC | |
| UTR Pro Newport Beach | 01/07 18:45 | - | Gabriel Jessup v Mark Kneiss | CANC | |
| UTR Pro Newport Beach | 01/07 18:45 | - | Gabriel Jessup v Rishvanth Krishna | CANC | |
| UTR Pro Newport Beach | 01/07 02:30 | - | Gabriel Jessup v Maciej Rajski | 5-7,2-6 | |
| UTR Pro Newport Beach | 01/06 03:00 | - | David Duong v Gabriel Jessup | 6-2,3-6,6-3 | |
| UTR Pro Boca Raton | 11/08 19:00 | 28 | Gabriel Jessup v Sutton Severance | Walkover | |
| UTR Pro Boca Raton | 11/07 18:00 | 27 | Gabriel Jessup v Elie Elie Azoulay | 7-6,6-4 | |
| UTR Pro Boca Raton | 11/05 21:55 | - | Gabriel Jessup v Maddox Bose | 6-4,7-5 | |
| UTR Pro Boca Raton | 11/05 19:10 | - | Gabriel Jessup v Vanja Hodzic | CANC | |
| UTR Pro Boca Raton | 11/04 22:05 | - | Gabriel Jessup v Thomas Machado | 6-3,2-6,1-6 | |
| UTR Pro Boca Raton | 11/03 15:00 | - | Gabriel Jessup v Hugo Car | 3-6,4-6 | |
| UTR Pro Stockton | 05/06 17:00 | - | Gabriel Jessup v Tiago Silva | CANC |