Stadium: Court 9 Round: 62 Ground: Clay
| ITF M25 Columbus | 2021/11/17 14:55 | Drew Van Orderlain v Roy Smith | 4-6,7-6,4-6 |
| ITF M25 Columbus | 2021/11/16 14:55 | Jonathan Sorbo v Drew Van Orderlain | 4-6,0-6 |
| ITF M25 Columbus | 2021/11/15 13:00 | Drew Van Orderlain v Yang Liu | 6-3,6-2 |
| ITF M15 Heraklion | 2021/11/07 12:00 | Kai Lemstra v Drew Van Orderlain | 6-2,6-3 |
| ITF M15 Heraklion | 2021/11/01 11:00 | Drew Van Orderlain v Christian Fellin | 6-3,2-6,6-10 |
| UTR Pro Tennis Series Copenhagen | 2021/10/24 08:30 | Henrik Heise Korsgaard v Drew Van Orderlain | 3-6,7-6,6-2 |
| UTR Pro Tennis Series Copenhagen | 2021/10/20 10:00 | Drew Van Orderlain v Alexander Stage | 6-4,3-6,6-3 |
| UTR Pro Tennis Series Copenhagen | 2021/10/19 08:30 | Drew Van Orderlain v Marius Ruzgas | 3-6,4-6 |