Stadium: Court 6 Round: 26 Ground: Clay
| ITF M15 Pittsburgh | 2019/07/02 14:00 | Michal Wozniak v Cleeve Harper | 2-6,4-6 |
| ITF M15 Pittsburgh | 2019/07/01 14:00 | Langford Hills v Cleeve Harper | 4-6,6-1,5-10 |
| ITF M15 Rochester | 2019/06/24 17:00 | David Volfson v Cleeve Harper | 6-0,6-0 |
| ITF M25 Tulsa | 2019/06/17 15:00 | Cleeve Harper v Andrew Fenty | 4-6,6-4,6-10 |
| ITF M15 Cancun | 2019/06/10 18:00 | Cleeve Harper v Kamen Damov | 7-6,3-6,5-10 |
| ITF M15 Cancun | 2019/06/10 13:30 | Skyler Butts v Cleeve Harper | 1-6,3-6 |
| ITF M15 Champaign | 2019/06/03 15:00 | Andrew Zhang v Cleeve Harper | 6-1,6-7,10-2 |
| ITF Canada F4 Qual | 2018/06/24 17:00 | Adrian Ortiz v Cleeve Harper | 5-7,7-5,6-3 |
| ITF M15 Pittsburgh | 2019/07/02 09:30 | Robby Shymansky v Paul Oosterbaan | 2-6,4-6 |
| ITF M15 Rochester | 2019/06/27 21:00 | Ronan Jachuck v Paul Oosterbaan | 2-6,7-6,6-2 |
| ITF M15 Rochester | 2019/06/26 21:30 | Dragos Constantin Ignat v Paul Oosterbaan | 4-6,6-7 |
| ITF M15 Orlando | 2019/06/21 14:00 | Strong Kirchheimer v Paul Oosterbaan | 6-0,6-3 |
| ITF M15 Orlando | 2019/06/20 16:00 | George Botezan v Paul Oosterbaan | 6-3,5-7,6-7 |
| ITF M15 Orlando | 2019/06/19 15:40 | Michael Shabaz v Paul Oosterbaan | 4-6,7-6,3-6 |
| ITF M15 Cancun | 2019/06/05 13:30 | Austin Rapp v Paul Oosterbaan | 3-6,6-4,7-5 |
| ITF M15 Cancun | 2019/05/28 13:30 | Paul Oosterbaan v Alejandro Gomez | 2-6,6-4,3-6 |