Stadium: Grandstand Round: 27 Ground: Clay
| ITF USA F21 | 2018/08/01 20:50 | Nicolas Alvarez v Paul Oosterbaan | 6-3,6-0 |
| ITF M25 Vero Beach | 2019/05/02 14:00 | Andrew Watson v Paul Oosterbaan | 4-6,3-6 |
| ITF M25 Vero Beach | 2019/05/01 18:00 | Jack Findel-Hawkins v Paul Oosterbaan | 2-6,6-7 |
| ITF M15 Orange Park | 2019/04/16 14:00 | Agustin Velotti v Paul Oosterbaan | 6-4,6-7,6-3 |
| ITF M15 Sunrise | 2019/04/09 15:00 | Paul Oosterbaan v Sandro Ehrat | 6-7,7-6,5-7 |
| ITF M15 Portimao | 2019/03/15 11:35 | Tiago Cacao v Paul Oosterbaan | 6-4,6-2 |
| ITF M15 Portimao | 2019/03/14 15:15 | Paul Oosterbaan v Lamine Ouahab | 6-2,7-6 |
| ITF M15 Portimao | 2019/03/12 11:00 | Simon A Ivanov v Paul Oosterbaan | 5-7,6-4,1-6 |
| ITF M15 Loule | 2019/03/07 15:30 | Sandro Ehrat v Paul Oosterbaan | 6-1,6-3 |
| ITF M25 Vero Beach | 2019/05/02 17:30 | Nick Chappell v Nicolas Alvarez | 6-7,1-6 |
| ITF M25 Vero Beach | 2019/05/01 18:25 | Felix Corwin v Nicolas Alvarez | 4-6,1-6 |
| ITF M15 Cancun | 2019/04/14 15:00 | Jordi Arconada v Nicolas Alvarez | 6-4,6-2 |
| ITF M15 Cancun | 2019/04/13 15:00 | Adam El Mihdawy v Nicolas Alvarez | 4-6,6-7 |
| ITF M15 Cancun | 2019/04/12 14:30 | Nicolas Alvarez v Gabriel Petit | 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 Quentin Robert | 6-2,4-6,7-6 |
| Davis Cup | 2019/04/06 21:25 | Kyle Johnson v Nicolas Alvarez | 3-6,2-6 |