| Challenger Drummondville | 11/10 00:45 | 14 | Jangjun Kim v Trey Hilderbrand | 6-1,6-1 | |
| Challenger Olbia | 10/12 10:35 | 14 |
[115] Trey Hilderbrand v
Enrico Dalla Valle
[465] 
|
5-7,4-6 | |
| Challenger Villena | 09/29 09:00 | 19 | [116] Trey Hilderbrand v Alberto B Campos [295] | 6-3,3-6,4-6 | |
| Challenger Villena | 09/28 09:00 | 14 | [409] Bernabe Z Miralles v Trey Hilderbrand [116] | 6-7,2-6 | |
| Challenger Saint-Tropez | 09/16 14:05 | 25 |
[143] Trey Hilderbrand v
Hugo Grenier
[199] 
|
4-6,1-6 | |
| Challenger Saint-Tropez | 09/15 11:30 | 19 | [143] Trey Hilderbrand v Aryan Shah [401] | 7-6,6-4 | |
| Challenger Saint-Tropez | 09/14 12:15 | 14 | Maxence Bertimon v Trey Hilderbrand | 1-6,5-7 | |
| Challenger Chicago | 08/04 16:00 | 19 | [240] Joshua Sheehy v Trey Hilderbrand [118] | 6-3,7-6 | |
| Challenger Chicago | 08/03 15:00 | 45 |
Trey Hilderbrand v
Adhithya Ganesan
|
6-2,3-6,7-5 | |
| Challenger Lexington | 07/27 15:45 | 14 |
[115] Trey Hilderbrand v
Martin Damm
[440] 
|
3-6,4-6 | |
| Challenger Newport | 07/08 19:35 | 25 | [120] Trey Hilderbrand v Tyler Zink [311] | 6-4,4-6,3-6 | |
| Challenger Newport | 07/07 15:30 | 19 | Trey Hilderbrand v Matt Kuhar | 4-6,6-4,7-5 | |
| Challenger Newport | 07/06 15:00 | 14 | Trey Hilderbrand v Boris Kozlov | 6-2,6-3 | |
| Challenger Tyler | 06/03 15:00 | 25 |
[367] Yi Zhou
v
Trey Hilderbrand [117] |
6-1,6-4 | |
| Challenger Tyler | 06/02 15:00 | 19 | Trey Hilderbrand v Braden Shick | 4-6,6-4,7-6 | |
| Challenger Tyler | 06/01 18:40 | 14 | [397] Nicolas Kicker v Trey Hilderbrand [117] | Retired | |
| Challenger Morelos | 03/30 17:55 | 14 | Robin Catry v Trey Hilderbrand | 6-1,6-3 | |
| Challenger Morelia | 03/23 22:00 | 14 |
[283] Aidan Mayo
v
Trey Hilderbrand [133] |
Retired | |
| Challenger Merida | 03/18 18:45 | 25 |
Trey Hilderbrand v
Alex Hernandez
|
4-6,2-6 | |
| Challenger Merida | 03/17 19:00 | 19 | Trey Hilderbrand v Nicolas Villalon | 6-2,6-4 | |
| Challenger Merida | 03/16 21:20 | 14 | Trey Hilderbrand v Diego Bustamante | 6-0,6-2 | |
| Challenger San Diego | 02/24 18:00 | 19 | Blaise Bicknell v Trey Hilderbrand | 6-4,6-3 | |
| Challenger San Diego | 02/23 20:55 | 14 | Jagger Leach v Trey Hilderbrand | 3-6,6-7 | |
| Challenger Cleveland | 01/29 16:00 | 26 |
[186] James Trotter
v
Trey Hilderbrand [145] |
6-7,6-2,6-4 | |
| Challenger Cleveland | 01/28 16:50 | 25 | [463] Nathan Ponwith v Trey Hilderbrand [145] | 6-7,6-4,0-6 | |
| Challenger Cleveland | 01/27 18:40 | 19 | [126] JJ Tracy v Trey Hilderbrand [145] | 6-7,6-4,2-6 | |
| Challenger Cleveland | 01/26 22:10 | 14 | Matt Kuhar v Trey Hilderbrand | 4-6,6-4,4-6 | |
| Challenger Oeiras | 01/07 14:20 | 25 | [307] Frederico Ferreira Silva v Trey Hilderbrand [164] | 6-7,6-2,6-4 | |
| Challenger Oeiras | 01/06 11:00 | 19 | [164] Trey Hilderbrand v Kaichi Uchida [366] | 6-2,2-6,6-2 | |
| Challenger Oeiras | 01/05 14:30 | 14 |
[307] Cezar Cretu
v
Trey Hilderbrand [162] |
7-6,4-6,4-6 |
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