| ITF - M15 Cancun | 06/10 18:00 | 54 | Cleeve Harper v Kamen Damov | 7-6,3-6,5-10 | |
| ITF - M15 Cancun | 06/10 13:30 | 54 | Skyler Butts v Cleeve Harper | 1-6,3-6 | |
| ITF - M15 Champaign | 06/03 15:00 | 54 | Andrew Zhang v Cleeve Harper | 6-1,6-7,10-2 | |
| ITF Canada F4 Qual | 06/24 17:00 | 44 | Adrian Ortiz v Cleeve Harper | 5-7,7-5,6-3 | |
| ITF Canada F3 Qual | 06/18 17:35 | 44 | A.J Catanzariti v Cleeve Harper | 6-3,6-3 |