Stadium: Court 8 Round: 25 Ground: Clay
| 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 |
| Orlando, Singles Qualifying M-ITF-USA-17A | 2019/06/19 15:40 | Shabaz, Michael v C. Oosterbaan, Paul | 4-6,7-6,3-6 |
| ITF M15 Cancun | 2019/06/05 13:30 | Rapp, Austin v C. Oosterbaan, Paul | 3-6,6-4,7-5 |
| ITF M15 Cancun | 2019/05/28 13:30 | C. Oosterbaan, Paul v Gomez, Alejandro | 2-6,6-4,3-6 |
| ITF - M25 Pensacola | 2019/05/09 15:00 | Gomez, Alejandro v C. Oosterbaan, Paul | 6-2,7-6 |