Stadium: Court 10 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Pittsburgh | 2019/07/06 17:00 | Paul Oosterbaan v Simon Freund | 1-6,1-6 |
| 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 |
| Challenger Winnetka | 2019/07/10 18:25 | John McNally v Guido Andreozzi | 5-7,1-6 |
| Challenger Winnetka | 2019/07/09 18:35 | John McNally v Sam Riffice | 6-4,4-6,6-4 |
| Challenger Winnetka | 2019/07/08 15:00 | John McNally v Volodymyr Uzhylovskyi | 6-3,6-2 |
| ITF M25 Tulsa | 2019/06/21 15:00 | Maxime Cressy v John McNally | 6-7,7-6,6-4 |
| ITF M25 Tulsa | 2019/06/20 15:00 | George Goldhoff v John McNally | 6-7,6-4,6-7 |
| ITF M25 Tulsa | 2019/06/18 20:35 | John McNally v Harrison Adams | 6-3,6-3 |
| Challenger Columbus | 2019/06/12 18:10 | Duckhee Lee v John McNally | 6-3,7-5 |
| Challenger Columbus | 2019/06/11 20:50 | Orlando Luz v John McNally | 5-7,7-6,5-7 |