| ITF M25 Weston | 01/31 18:00 | 26 | Dmitry Popko v Paul C Oosterbaan | 6-2,6-2 | |
| ITF M25 Weston | 01/30 15:00 | 25 | Paul C Oosterbaan v Adrian Obert | 6-4,6-4 | |
| ITF M25 Weston | 01/29 14:30 | 45 | Paul C Oosterbaan v Lucas Renard | 4-6,6-1,10-4 | |
| ITF M25 Weston | 01/28 14:30 | 45 | Paul Oosterbaan v Boris Arias | 6-2,6-4 | |
| ITF M25 Palm Coast | 01/25 15:00 | 27 | Paul C Oosterbaan v Or Ram-Harel | 2-6,1-6 | |
| ITF M25 Palm Coast | 01/24 18:00 | 26 | Paul C Oosterbaan v Matic Spec | 6-2,6-4 | |
| ITF M25 Palm Coast | 01/22 15:00 | 25 | Alejandro Gomez v Paul C Oosterbaan | 4-6,1-6 | |
| ITF M15 Naples | 01/15 18:30 | 25 | Dmitry Popko v Paul C Oosterbaan | 4-6,6-3,6-3 | |
| ITF USA F35 | 12/05 21:10 | 26 | Justin Roberts v Paul C Oosterbaan | 7-6,7-6 | |
| ITF USA F35 | 12/03 15:00 | 25 | Paul C Oosterbaan v Alex Knaff | 7-6,6-4 | |
| ITF USA F33 | 11/21 17:50 | 26 | Paul C Oosterbaan v Pavel Krainik | 4-6,3-6 | |
| ITF USA F33 | 11/20 17:40 | 25 | Diego Hidalgo v Paul Oosterbaan | 6-7,7-5,3-6 | |
| ITF USA F31 | 11/14 15:00 | 25 | Ferran Calvo Eman v Paul C Oosterbaan | 6-1,5-7,6-3 | |
| ITF Vietnam F5 | 10/30 03:00 | 25 | Roman Safiullin v Paul C Oosterbaan | 6-3,7-5 | |
| ITF Vietnam F4 | 10/26 02:30 | 27 | Nam Hoang Ly v Paul C Oosterbaan | 6-1,6-4 | |
| ITF Vietnam F4 | 10/25 04:25 | 26 | Paul C Oosterbaan v Jayesh Pungliya | 6-4,6-0 | |
| ITF Vietnam F4 | 10/23 02:30 | 25 | Paul C Oosterbaan v Lukas Ollert | Retired | |
| ITF USA F26 | 09/28 18:50 | 27 | Paul C Oosterbaan v Strong Kirchheimer | 2-6,3-6 | |
| ITF USA F26 | 09/27 18:45 | 26 | Paul C Oosterbaan v Trent Bryde | 6-3,6-2 | |
| ITF USA F26 | 09/25 19:40 | 25 | Paul C Oosterbaan v Aleksandre Bakshi | 7-5,6-1 | |
| ITF USA F25 | 09/20 17:00 | 26 | Alan Kohen v Paul C Oosterbaan | 2-6,6-1,6-2 | |
| ITF USA F25 | 09/19 19:15 | 25 | Isaiah Strode v Paul C Oosterbaan | 6-7,6-7 | |
| ITF USA F24 | 09/13 16:30 | 26 | Paul C Oosterbaan v Daniel Cukierman | 3-6,0-6 | |
| ITF USA F24 | 09/11 16:30 | 25 | Paul C Oosterbaan v Conor Berg | 6-4,6-3 | |
| ITF USA F23 | 08/14 15:35 | 25 | Antoine Hoang v Paul C Oosterbaan | 6-3,7-6 | |
| ITF USA F22 | 08/10 16:00 | 27 | Paul C Oosterbaan v Sebastian Korda | 6-4,4-6,0-6 | |
| ITF USA F22 | 08/09 15:05 | 26 | Michael Redlicki v Paul C Oosterbaan | 3-6,2-6 | |
| ITF USA F22 | 08/08 17:10 | 25 | Luis Patino v Paul Oosterbaan | 1-6,3-6 | |
| ITF USA F21 | 08/01 20:50 | 25 | Nicolas Alvarez v Paul C Oosterbaan | 6-3,6-0 | |
| Challenger Winnetka Qual | 07/07 15:00 | 45 | Paul Oosterbaan v Logan Smith | 1-6,5-7 |