Stadium: Court 8 Round: 25 Ground: Clay
| 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 |
| ITF M25 Pensacola | 2019/05/09 15:00 | Alejandro Gomez v Paul Oosterbaan | 6-2,7-6 |