Stadium: Grandstand Round: 27 Ground: Clay
| ITF USA F21 | 2018/08/01 20:50 | Nicolas Alvarez v C. Oosterbaan, Paul | 6-3,6-0 |
| Vero Beach, Fl, Singles Qualifying M-ITF-USA-17A | 2019/05/02 14:00 | Watson, Andrew v C. Oosterbaan, Paul | 4-6,3-6 |
| Vero Beach, Fl, Singles Qualifying M-ITF-USA-17A | 2019/05/01 18:00 | Findel-Hawkins, Jack v C. Oosterbaan, Paul | 2-6,6-7 |
| ITF - M15 Orange Park | 2019/04/16 14:00 | Velotti, Agustin v C. Oosterbaan, Paul | 6-4,6-7,6-3 |
| ITF - M15 Sunrise | 2019/04/09 15:00 | C. Oosterbaan, Paul v Ehrat, Sandro | 6-7,7-6,5-7 |
| Portimao, Singles Qualifying M-ITF-POR-16A | 2019/03/15 11:35 | Cacao, Tiago v C. Oosterbaan, Paul | 6-4,6-2 |
| Portimao, Singles Qualifying M-ITF-POR-16A | 2019/03/14 15:15 | C. Oosterbaan, Paul v Ouahab, Lamine | 6-2,7-6 |
| Portimao, Singles Qualifying M-ITF-POR-16A | 2019/03/12 11:00 | Ivanov, Simon Anthony v C. Oosterbaan, Paul | 5-7,6-4,1-6 |
| ITF M15 Loule | 2019/03/07 15:30 | Ehrat, Sandro v C. Oosterbaan, Paul | 6-1,6-3 |
| Vero Beach, Fl, Singles Qualifying M-ITF-USA-17A | 2019/05/02 17:30 | Nick Chappell v Nicolas Alvarez | 6-7,1-6 |
| Vero Beach, Fl, Singles Qualifying M-ITF-USA-17A | 2019/05/01 18:25 | Felix Corwin v Nicolas Alvarez | 4-6,1-6 |
| ITF M15 Cancun | 2019/04/14 15:00 | Arconada, Jordi v Nicolas Alvarez | 6-4,6-2 |
| ITF M15 Cancun | 2019/04/13 15:00 | El Midhawy, Adam v Nicolas Alvarez | 4-6,6-7 |
| ITF M15 Cancun | 2019/04/12 14:30 | Nicolas Alvarez v Petit, Gabriel | 6-7,7-5,6-3 |
| ITF M15 Cancun | 2019/04/11 17:50 | Nicolas Alvarez v Yshai Oliel | 6-3,6-4 |
| ITF M15 Cancun | 2019/04/10 13:45 | Nicolas Alvarez v Robert, Quentin | 6-2,4-6,7-6 |
| Coupe Davis | 2019/04/06 21:25 | Johnson, Kyle v Nicolas Alvarez | 3-6,2-6 |