| UTR Pro Florida | 2023/10/03 16:30 | Trey Hilderbrand v Emmett Ward | 6-3,6-1 |
| UTR Pro Florida | 2023/10/02 18:00 | Trey Hilderbrand v Kurt Miller | 6-3,3-6,6-3 |
| ITF M25 Setubal | 2023/09/20 09:00 | Aidan Mchugh v Trey Hilderbrand | 6-1,6-3 |
| ITF M25 Setubal | 2023/09/19 10:30 | Trey Hilderbrand v Alfredo Casso | 6-3,6-3 |
| ITF M25 Setubal | 2023/09/18 09:00 | Trey Hilderbrand v David Munoz | 6-3,6-0 |
| ITF M25 Sintra | 2023/09/13 09:00 | Trey Hilderbrand v Duarte Vale | 4-6,3-6 |
| ITF M25 Sintra | 2023/09/08 09:25 | Trey Hilderbrand v Jaime Faria | 2-6,3-6 |
| ITF M25 Sintra | 2023/09/07 10:00 | Trey Hilderbrand v Leopold Zima | 6-1,3-6,6-4 |
| UTR Pro Florida | 2023/10/03 18:00 | Kurt Miller v Gerard Escandell | 1-6,6-3,6-2 |