| UTR Pro Boston | 2023/07/13 18:00 | Jackson Ross v Aman Sharma | 6-3,6-1 |
| UTR Pro Boston | 2023/07/12 18:00 | Baptiste Anselmo v Jackson Ross | 4-6,4-6 |
| UTR Pro Boston | 2023/07/11 18:00 | James Lian v Jackson Ross | 4-6,7-6,4-6 |
| UTR Pro Florida | 2023/07/07 15:01 | Jackson Ross v Jerry Barton | 4-6,2-6 |
| UTR Pro Florida | 2023/07/05 12:00 | Jackson Ross v Matthew Rankin | 6-2,6-4 |
| UTR Pro Florida | 2023/07/04 18:35 | Jackson Ross v Vignesh Gogineni | 6-4,5-3 |
| UTR Pro Florida | 2023/07/03 16:26 | Gabriel Hurtado v Jackson Ross | 7-5,6-1 |
| UTR Pro Florida | 2023/07/02 18:13 | Jackson Ross v Sylvestre Monnou | 6-1,6-1 |
| UTR Pro Boston | 2023/07/13 19:30 | Baptiste Anselmo v James Hopper | 6-7,2-6 |
| UTR Pro Boston | 2023/07/13 00:15 | James Lian v James Hopper | 2-6,2-6 |
| UTR Pro Boston | 2023/07/10 20:05 | Aman Sharma v James Hopper | 2-6,7-6,4-5 |
| UTR Pro Florida | 2023/06/25 14:30 | James Hopper v Luka Butera | 6-3,1-6,1-0 |
| UTR Pro Florida | 2023/06/24 16:30 | James Hopper v Stefan Storch | 6-0,6-4 |
| UTR Pro Florida | 2023/06/23 13:00 | James Hopper v Welsh Hotard | 3-6,4-6 |
| UTR Pro Florida | 2023/06/21 15:00 | James Hopper v Lucas Silva | 6-1,6-3 |
| UTR Pro Florida | 2023/06/20 13:00 | James Hopper v Spencer Gray | 7-5,4-6,0-6 |