Stadium: Court 8 Round: 28 Ground: Clay
| ITF M15 - Pittsburgh | 2019/07/05 18:30 | Maksim Tikhomirov v Paul Oosterbaan | 4-6,5-7 |
| ITF M15 - Pittsburgh | 2019/07/04 16:15 | Cleeve Harper v Paul Oosterbaan | 3-6,3-6 |
| 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 - Pittsburgh | 2019/07/04 15:25 | Simon Freund v Ricardo Rodriguez-Pace | 3-6,6-1,7-5 |
| ITF M15 - Pittsburgh | 2019/07/02 14:00 | John Harrison Richmond v Simon Freund | 4-6,3-6 |
| ITF M15 - Rochester | 2019/06/29 19:00 | Simon Freund v Strong Kirchheimer | 1-6,5-7 |
| ITF M15 - Rochester | 2019/06/28 18:15 | Simon Freund v Ronan Jachuck | 6-2,6-4 |
| ITF M15 - Rochester | 2019/06/27 18:40 | Simon Freund v Zachary Svajda | 6-4,0-6,6-3 |
| ITF M15 - Rochester | 2019/06/26 20:15 | Maksim Tikhomirov v Simon Freund | 6-3,4-6,3-6 |
| ITF M25 - Tulsa | 2019/06/19 15:00 | Martin Redlicki v Simon Freund | 6-4,6-3 |
| ITF M25 - Tulsa | 2019/06/18 15:00 | Simon Freund v Abraham Asaba | 6-2,6-3 |