Stadium: Stadium Round: 26 Ground: Hardcourt outdoor
| ITF USA F24 | 2018/09/11 16:30 | Paul Oosterbaan v Conor Berg | 6-4,6-3 |
| 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 USA F24 | 2018/09/12 20:30 | Daniel Cukierman v Michael Shabaz | 6-3,6-3 |
| ITF Israel F8 | 2018/06/06 09:05 | Ugo Humbert v Daniel Cukierman | 6-2,6-1 |
| ITF Israel F8 | 2018/06/05 11:00 | Daniel Cukierman v Dan Added | 7-6,6-3 |
| ITF USA F2 | 2018/01/12 18:00 | Daniel Cukierman v Kaichi Uchida | 0-6,2-6 |
| ITF USA F2 | 2018/01/11 20:35 | Daniel Cukierman v Karue Sell | 7-6,6-1 |
| ITF USA F2 | 2018/01/11 02:10 | Evan Song v Daniel Cukierman | 3-6,1-6 |
| ITF USA F2 Qual | 2018/01/10 18:00 | Daniel Cukierman v Alexander Lebedev | 6-4,6-4 |
| ITF USA F2 Qual | 2018/01/07 18:00 | Jared Hiltzik v Daniel Cukierman | 2-6,4-6 |