Stadium: Court 4 Ground: Hardcourt outdoor
| ITF M15 Cancun | 2021/12/13 17:00 | Masamichi Imamura v Cleeve Harper | 6-4,6-4 |
| ITF M15 Cancun | 2021/12/05 14:00 | Daniel Antonio Nunez v Cleeve Harper | 6-2,3-6,16-14 |
| ITF M15 Cancun | 2021/11/28 14:00 | Daniel Antonio Nunez v Cleeve Harper | 7-5,6-2 |
| ITF M25 Austin | 2021/11/15 17:00 | Cleeve Harper v Chris Rodesch | 0-6,1-6 |
| UTR Pro Tennis Series Atlanta | 2021/07/16 12:00 | Cleeve Harper v Aidan Kim | 6-2,1-1 |
| UTR Pro Tennis Series Atlanta | 2021/07/15 12:00 | Cleeve Harper v Alan Sau Franco | 6-3,5-2 |
| UTR Pro Tennis Series Atlanta | 2021/07/12 13:30 | Lukas Greif v Cleeve Harper | 7-6,5-7,3-5 |
| ITF M15 Weston | 2021/07/02 15:10 | Cleeve Harper v Nicolas Mejia | 3-6,4-6 |
| ITF M25 Santo Domingo | 2022/02/21 15:00 | Henry Patten v Drew Van Orderlain | 6-4,6-4 |
| ITF M25 Santo Domingo | 2022/02/20 14:00 | Juan Sebastian Osorio v Drew Van Orderlain | 3-6,1-6 |
| ITF M25 Punta del Este | 2022/02/07 15:00 | Jordi Garcia Mestre v Drew Van Orderlain | 6-0,7-5 |
| ITF M25 Campos do Jordao | 2022/01/31 14:00 | Gabriel P Tumasonis v Drew Van Orderlain | 7-6,6-3 |
| ITF M25 Weston | 2022/01/24 17:00 | Mikel Anderson v Drew Van Orderlain | 6-7,6-2,10-6 |
| ITF M25 Weston | 2022/01/23 15:15 | Uladzislau Tarasevich v Drew Van Orderlain | 3-6,2-6 |
| 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 |