| ITF Canada F4 | 06/27 18:40 | 25 | Ortiz, Adrian v C. Oosterbaan, Paul | 7-5,6-3 | |
| ITF Canada F3 | 06/24 20:00 | 29 | Thai-Son Kwiatkowski v C. Oosterbaan, Paul | 6-4,6-3 | |
| ITF Canada F3 | 06/24 16:00 | 28 | Aguilar, Juan Carlos v C. Oosterbaan, Paul | 5-7,6-3,5-7 | |
| ITF Canada F3 | 06/22 17:00 | 27 | C. Oosterbaan, Paul v Monette, Samuel | 2-6,6-4,6-4 | |
| ITF Canada F3 | 06/21 19:45 | 26 | Lopez Villasenor, Gerardo v C. Oosterbaan, Paul | 6-7,6-7 | |
| ITF Canada F3 | 06/19 20:35 | 25 | C. Oosterbaan, Paul v Day, Alexander | 6-2,6-3 | |
| ITF Turkey F22 | 06/06 07:30 | 25 | Mert Naci Turker v C. Oosterbaan, Paul | 3-6,6-1,6-4 | |
| ITF Turkey F22 | 06/04 07:30 | 62 | Irigaray Guarne, Pablo v C. Oosterbaan, Paul | 2-6,6-3,1-6 | |
| ITF Turkey F22 | 06/03 07:30 | 62 | Gorgun, Omer Berk v C. Oosterbaan, Paul | 0-6,0-6 | |
| ITF Turkey F21 Qual | 05/28 07:30 | 62 | Aleksandre Metreveli v C. Oosterbaan, Paul | 3-6,6-4,6-2 | |
| ITF Turkey F21 Qual | 05/27 09:00 | 62 | Tadas Babelis v C. Oosterbaan, Paul | 4-6,4-6 | |
| ITF Turkey F21 Qual | 05/26 10:00 | 62 | Pirolt, Pietro v C. Oosterbaan, Paul | 1-6,2-6 | |
| Challenger Savannah Qual | 04/29 14:00 | 46 | C. Oosterbaan, Paul v Redlicki, Michael | 3-6,6-3,6-7 | |
| Challenger Savannah Qual | 04/28 14:00 | 45 | Stice, Tyler v C. Oosterbaan, Paul | 5-7,6-2,1-6 | |
| ITF USA F11 | 04/19 16:15 | 26 | Jose Pereira v C. Oosterbaan, Paul | 6-1,6-2 | |
| ITF USA F11 | 04/18 16:05 | 25 | Bradley, Julian v C. Oosterbaan, Paul | 5-7,6-3,0-6 | |
| ITF USA F11 | 04/16 15:00 | 60 | Emmett Ward v C. Oosterbaan, Paul | 2-6,2-6 | |
| ITF USA F11 | 04/15 14:00 | 60 | Noah Schachter v C. Oosterbaan, Paul | 4-6,4-6 | |
| ITF USA F11 | 04/14 18:00 | 60 | C. Oosterbaan, Paul v Jesse Flores | 6-4,6-4 | |
| ITF USA F11 | 04/13 18:00 | 60 | Lewis, Edward v C. Oosterbaan, Paul | 0-6,2-6 | |
| ITF USA F10 Qual | 04/10 15:00 | 62 | C. Oosterbaan, Paul v Bourchier, Edward | 4-6,6-7 | |
| ITF USA F10 Qual | 04/09 15:00 | 62 | C. Oosterbaan, Paul v Pulliam, Jack | 6-1,6-0 | |
| ITF USA F10 Qual | 04/08 18:30 | 62 | Francesco Ferrari v C. Oosterbaan, Paul | 3-6,3-6 | |
| ITF USA F6 | 01/27 15:00 | 60 | Fernando Yamacita v C. Oosterbaan, Paul | 6-1,5-7,6-7 | |
| ITF USA F23 | 06/29 16:05 | 25 | Cameron Norrie v C. Oosterbaan, Paul | 6-3,6-1 | |
| ITF USA F21 | 06/25 14:00 | 28 | Ryan Haviland v C. Oosterbaan, Paul | 5-7,6-2,6-3 | |
| ITF USA F21 | 06/24 15:25 | 27 | El Midhawy, Adam v C. Oosterbaan, Paul | 3-6,6-4,3-6 | |
| ITF USA F21 | 06/23 14:00 | 26 | C. Oosterbaan, Paul v Bangoura, Sekou | 7-6,6-4 | |
| ITF USA F21 Qual | 06/20 14:00 | 62 | Spec, Matic v C. Oosterbaan, Paul | 4-6,4-6 | |
| ITF USA F21 Qual | 06/19 14:00 | 62 | Woog, Jarryd v C. Oosterbaan, Paul | 4-6,3-6 |