Stadium: Court 1 Round: 25 Ground: Hardcourt indoor
| 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 |
| UTR Pro Tennis Series Copenhagen | 2021/10/18 08:30 | Drew Van Orderlain v Adam Heinonen | 4-6,5-7 |
| ITF M15 Ithaca | 2021/11/05 15:15 | Roy Smith v Cannon Kingsley | 4-6,2-6 |
| ITF M15 Ithaca | 2021/11/04 17:15 | Roy Smith v Dan Martin | 6-1,6-2 |
| ITF M15 Ithaca | 2021/11/03 13:55 | Roy Smith v Ishaan Ravichander | 6-3,6-4 |
| Challenger Las Vegas | 2021/10/24 17:00 | Nick Chappell v Roy Smith | 7-6,6-7,6-2 |
| ITF M15 Cancun | 2021/10/12 17:00 | Roy Smith v Jesse Flores | 4-6,2-6 |
| ITF M15 Ithaca | 2021/10/06 18:35 | Roy Smith v Ryan Shane | 5-7,3-6 |
| ITF M15 Castelo Branco | 2021/07/29 14:05 | Clement Chidekh v Roy Smith | 6-4,7-5 |
| ITF M15 Castelo Branco | 2021/07/28 15:30 | Ben Jones v Roy Smith | 1-6,4-6 |