Stadium: Court 10 Round: 54 Ground: Hardcourt outdoor
| Challenger Drummondville | 2023/11/12 20:35 | Luca Wiedenmann v Trey Hilderbrand | 6-3,4-6,6-4 |
| ITF - Harlingen M25 | 2023/10/26 19:20 | Trey Hilderbrand v Raphael Perot | 4-6,4-6 |
| ITF - Harlingen M25 | 2023/10/25 16:00 | Giulio Perego v Trey Hilderbrand | 4-6,0-6 |
| ITF - Las Vegas M15 | 2023/10/18 19:45 | Trey Hilderbrand v Johannus Monday | 2-6,6-7 |
| ITF - Las Vegas M25 | 2023/10/17 13:00 | Guy Orly Iradukunda v Trey Hilderbrand | 1-6,4-6 |
| ITF - Las Vegas M25 | 2023/10/16 13:00 | Taiyo Hirano v Trey Hilderbrand | 3-6,4-6 |
| UTR Pro - Floryda | 2023/10/07 16:30 | Joao Graca v Trey Hilderbrand | 4-6,6-0,6-3 |
| UTR Pro - Floryda | 2023/10/05 18:37 | Trey Hilderbrand v Andrew Delgado | 1-6,7-5,6-1 |
| ITF - Ithaca M25 | 2024/01/17 17:00 | Henrik Wiersholm v Drew Van Orderlain | 6-3,6-2 |
| ITF - Ithaca M25 | 2024/01/16 15:30 | Noah Eisenberg v Drew Van Orderlain | 1-6,0-6 |
| ITF - Ithaca M25 | 2024/01/15 15:00 | Jack McCarthy v Drew Van Orderlain | 4-6,2-6 |
| Challenger Calgary | 2023/11/05 19:55 | Drew Van Orderlain v Ryan Seggerman | 4-6,4-6 |
| ITF - Edmonton M25 | 2023/10/31 17:20 | Nicolas Kotzen v Drew Van Orderlain | 6-2,6-4 |
| ITF - Edmonton M25 | 2023/10/30 18:55 | Drew Van Orderlain v Frederick McRae | 6-0,6-0 |
| ITF - Edmonton M25 | 2023/10/29 18:10 | Drew Van Orderlain v Igor Danich | 4-6,6-3,10-3 |
| ITF - Saint-Augustin M25 | 2023/10/25 18:25 | Drew Van Orderlain v Junghee You | 4-6,6-1,5-7 |