Stadium: Court 16 Round: 25 Ground: Hardcourt outdoor
| ITF USA F23 | 2018/08/14 15:35 | Antoine Hoang v Paul Oosterbaan | 6-3,7-6 |
| ITF USA F22 | 2018/08/10 16:00 | Paul Oosterbaan v Sebastian Korda | 6-4,4-6,0-6 |
| ITF USA F22 | 2018/08/09 15:05 | Michael Redlicki v Paul Oosterbaan | 3-6,2-6 |
| ITF USA F22 | 2018/08/08 17:10 | Luis Patino v Paul Oosterbaan | 1-6,3-6 |
| ITF USA F21 | 2018/08/01 20:50 | Nicolas Alvarez v Paul Oosterbaan | 6-3,6-0 |
| Challenger Winnetka Qual | 2018/07/07 15:00 | Paul Oosterbaan v Logan Smith | 1-6,5-7 |
| ITF Canada F4 | 2018/06/27 18:40 | Adrian Ortiz v Paul Oosterbaan | 7-5,6-3 |
| ITF Canada F3 | 2018/06/24 20:00 | Thai-Son Kwiatkowski v Paul Oosterbaan | 6-4,6-3 |
| ITF Belarus F3 | 2018/08/19 11:30 | Conor Berg v Ben Jones | 6-3,6-7,5-7 |
| ITF Belarus F2 | 2018/08/15 09:40 | Conor Berg v Sergey Betov | 6-7,5-7 |
| ITF Belarus F2 | 2018/08/13 07:00 | Conor Berg v Ryan James Storrie | 6-3,3-6,7-6 |
| ITF Belarus F2 | 2018/08/12 07:00 | Conor Berg v Dzianis Zharyn | 6-4,6-2 |
| ITF Belarus F2 | 2018/08/11 07:00 | Conor Berg v Artsiom Cherkasau | 6-0,6-0 |
| ITF Belarus F1 | 2018/08/07 07:00 | Yan Bondarevskiy v Conor Berg | 6-2,7-5 |
| ITF Ireland F1 | 2018/08/03 12:40 | Joshua Paris v Conor Berg | 6-3,6-4 |
| ITF Ireland F1 | 2018/08/02 12:20 | Lucas Renard v Conor Berg | 2-6,6-3,5-7 |