Stadium: Court 10 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Pittsburgh | 2019/07/06 17:00 | C. Oosterbaan, Paul v Simon Freund | 1-6,1-6 |
| ITF M15 Pittsburgh | 2019/07/05 18:30 | Tikhomirov, Maksim v C. Oosterbaan, Paul | 4-6,5-7 |
| ITF M15 Pittsburgh | 2019/07/04 16:15 | Harper, Cleeve v C. Oosterbaan, Paul | 3-6,3-6 |
| ITF M15 Pittsburgh | 2019/07/02 09:30 | Shymansky, Robby v C. Oosterbaan, Paul | 2-6,4-6 |
| Rochester, Singles M-ITF-USA-19A | 2019/06/27 21:00 | Jachuck, Ronan v C. Oosterbaan, Paul | 2-6,7-6,6-2 |
| Rochester, Singles M-ITF-USA-19A | 2019/06/26 21:30 | Ignat, Dragos Constantin v C. Oosterbaan, Paul | 4-6,6-7 |
| Orlando, Singles Qualifying M-ITF-USA-17A | 2019/06/21 14:00 | Strong Kirchheimer v C. Oosterbaan, Paul | 6-0,6-3 |
| Orlando, Singles Qualifying M-ITF-USA-17A | 2019/06/20 16:00 | Botezan, George v C. Oosterbaan, Paul | 6-3,5-7,6-7 |
| Winnetka, USA | 2019/07/10 18:25 | Mcnally, John v Guido Andreozzi | 5-7,1-6 |
| Winnetka, USA | 2019/07/09 18:35 | Mcnally, John v Riffice, Sam | 6-4,4-6,6-4 |
| Winnetka, USA | 2019/07/08 15:00 | Mcnally, John v Uzhylovsky, Vladimir | 6-3,6-2 |
| Tulsa, Singles Main, M-ITF-USA-16A | 2019/06/21 15:00 | Maxime Cressy v Mcnally, John | 6-7,7-6,6-4 |
| Tulsa, Singles Main, M-ITF-USA-16A | 2019/06/20 15:00 | George Goldhoff v Mcnally, John | 6-7,6-4,6-7 |
| Tulsa, Singles Main, M-ITF-USA-16A | 2019/06/18 20:35 | Mcnally, John v Harrison Adams | 6-3,6-3 |
| Challenger Columbus | 2019/06/12 18:10 | Duckhee Lee v Mcnally, John | 6-3,7-5 |
| Challenger Columbus | 2019/06/11 20:50 | Orlando Luz v Mcnally, John | 5-7,7-6,5-7 |