Stadium: Court 6 Round: 25 Ground: Hardcourt indoor
| ITF M15 Santo Domingo | 2023/11/17 15:00 | Henrik Wiersholm v Bruno Kuzuhara | 2-6,2-6 |
| ITF M15 Santo Domingo | 2023/11/16 16:30 | Henrik Wiersholm v Petro Orlando Fellin | 7-5,6-3 |
| ITF M15 Santo Domingo | 2023/11/15 17:50 | Henrik Wiersholm v Aydan Gomez Osorio | 6-3,6-1 |
| ITF M15 Santo Domingo | 2023/11/12 12:50 | Henrik Wiersholm v Bruno Kuzuhara | 4-6,6-1,5-10 |
| ITF M15 Santo Domingo | 2023/11/11 13:00 | Henrik Wiersholm v Alexander Vlahos | 6-1,6-3 |
| ITF M15 Santo Domingo | 2023/11/08 17:30 | Henrik Wiersholm v Lance A L Castelan | 5-7,6-0,6-2 |
| ITF M25 Cairns | 2023/10/10 08:25 | Henrik Wiersholm v Blake Ellis | 2-6,6-7 |
| ITF M25 Cairns | 2023/10/02 23:50 | Henrik Wiersholm v Matt Hulme | 3-6,2-6 |
| ITF M25 Ithaca | 2024/01/16 15:30 | Noah Eisenberg v Drew Van Orderlain | 1-6,0-6 |
| ITF M25 Ithaca | 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 M25 Edmonton | 2023/10/31 17:20 | Nicolas Kotzen v Drew Van Orderlain | 6-2,6-4 |
| ITF M25 Edmonton | 2023/10/30 18:55 | Drew Van Orderlain v Frederick McRae | 6-0,6-0 |
| ITF M25 Edmonton | 2023/10/29 18:10 | Drew Van Orderlain v Igor Danich | 4-6,6-3,10-3 |
| ITF M25 Saint-Augustin | 2023/10/25 18:25 | Drew Van Orderlain v Junghee You | 4-6,6-1,5-7 |
| ITF M25 Saint-Augustin | 2023/10/24 14:00 | Drew Van Orderlain v Henry Lieberman | 6-4,7-6 |