Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| ITF - M25 Pensacola | 2019/05/09 15:00 | Gomez, Alejandro v C. Oosterbaan, Paul | 6-2,7-6 |
| Palm Coast, Singles M-ITF-USA-05A | 2019/01/22 15:00 | Gomez, Alejandro v C. Oosterbaan, Paul | 4-6,1-6 |
| ITF - M25 Pensacola | 2019/05/09 15:00 | Gomez, Alejandro v C. Oosterbaan, Paul | 6-2,7-6 |
| ITF - M25 Pensacola | 2019/05/08 14:00 | Hamilton, Grey v C. Oosterbaan, Paul | 6-7,1-6 |
| Vero Beach, Fl, Singles Qualifying M-ITF-USA-17A | 2019/05/04 16:00 | Dmitry Popko v C. Oosterbaan, Paul | 6-2,6-1 |
| 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 |
| ITF M15 Cancun | 2019/05/22 15:35 | Gomez, Alejandro v Cozbinov, Alexander | 1-6,6-3,4-6 |
| ITF M15 Cancun | 2019/05/17 15:00 | El Midhawy, Adam v Gomez, Alejandro | 6-4,6-4 |
| ITF M15 Cancun | 2019/05/16 15:05 | Christian Langmo v Gomez, Alejandro | 6-7,2-6 |
| ITF M15 Cancun | 2019/05/15 15:45 | George Goldhoff v Gomez, Alejandro | 6-2,3-6,4-6 |
| ITF - M25 Pensacola | 2019/05/10 16:55 | Gomez, Alejandro v Harrison Adams | 6-7,6-3,4-6 |
| ITF - M25 Pensacola | 2019/05/09 15:00 | Gomez, Alejandro v C. Oosterbaan, Paul | 6-2,7-6 |
| ITF - M25 Pensacola | 2019/05/08 14:00 | Gomez, Alejandro v Nick Chappell | 6-1,6-3 |
| ITF - M25 Santa Margherita | 2019/04/16 14:30 | Gomez, Alejandro v Kirill Kivattsev | 0-6,2-6 |