Stadium: Court 3 Round: 25 Ground: Hardcourt outdoor
| ITF M25 Las Vegas | 2023/10/17 13:00 | Guy Orly Iradukunda v Trey Hilderbrand | 1-6,4-6 |
| ITF M25 Las Vegas | 2023/10/16 13:00 | Taiyo Hirano v Trey Hilderbrand | 3-6,4-6 |
| UTR Pro Florida | 2023/10/07 16:30 | Joao Graca v Trey Hilderbrand | 4-6,6-0,6-3 |
| UTR Pro Florida | 2023/10/05 18:37 | Trey Hilderbrand v Andrew Delgado | 1-6,7-5,6-1 |
| UTR Pro Florida | 2023/10/04 16:30 | Trey Hilderbrand v Gerard Escandell | 6-1,6-0 |
| 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 |
| Challenger Tiburon | 2023/10/04 18:00 | Johannus Monday v Alexander Ritschard | 3-6,7-6,6-7 |
| Challenger Tiburon | 2023/10/02 21:35 | Laurent Lokoli v Johannus Monday | 6-7,2-6 |
| Challenger Istanbul | 2023/09/06 10:25 | Johannus Monday v Jesper De Jong | 5-7,1-6 |
| Challenger Istanbul | 2023/09/04 11:30 | Johannus Monday v Kacper Zuk | 4-6,6-1,6-4 |
| Challenger Mallorca | 2023/08/29 12:00 | Marco Trungelliti v Johannus Monday | 6-4,6-4 |
| ITF M25 Aldershot | 2023/08/18 11:30 | Arthur Fery v Johannus Monday | 7-5,6-1 |
| ITF M25 Aldershot | 2023/08/17 08:55 | Ewen Lumsden v Johannus Monday | 4-6,4-6 |
| ITF M25 Aldershot | 2023/08/15 09:00 | Alec Beckley v Johannus Monday | 4-6,1-6 |