Round: 28 Ground: Hardcourt outdoor
| UTR Pro Boca Raton | 2025/03/30 14:00 | Ethan Schiffman v Gabriel Jessup | 6-2,6-2 |
| UTR Pro Boca Raton | 2025/03/29 16:10 | Gabriel Jessup v Ariel Meshulam | 6-3,4-6,7-6 |
| UTR Pro Boca Raton | 2025/03/28 19:45 | Gabriel Jessup v Dillon Blake | 6-0,6-4 |
| UTR Pro Boca Raton | 2025/03/26 18:00 | Gabriel Jessup v David Rieme | 4-6,6-1,6-3 |
| UTR Pro Boca Raton | 2025/03/25 15:00 | Gabriel Jessup v Jonathan Irwanto | 6-3,6-1 |
| UTR Pro Boca Raton | 2025/03/24 20:00 | Kalman Boyd v Gabriel Jessup | 5-7,6-3,6-4 |
| UTR Pro Winston-Salem | 2024/12/01 19:30 | Gabriel Jessup v Jamieson Nathan | 4-6,6-7 |
| UTR Pro Knoxville | 2024/09/08 14:30 | Wissam Abderrahman v Gabriel Jessup | 1-6,6-4,6-3 |