Stadium: EHS Court 7 Round: 26 Ground: Hardcourt outdoor
| Challenger Savannah Qual | 2018/04/29 14:00 | Paul Oosterbaan v Michael Redlicki | 3-6,6-3,6-7 |
| ITF USA F22 | 2018/08/08 20:05 | Michael Redlicki v Alexander Lebedev | 6-3,7-6 |
| ITF USA F20 Qual | 2018/07/22 15:00 | Michael Redlicki v Kyle Seelig | 6-3,1-6,2-6 |
| ITF USA F20 Qual | 2018/07/21 15:00 | Michael Redlicki v Justin Lunn | 6-2,6-1 |
| Challenger Winnetka Qual | 2018/07/08 15:00 | Martin Redlicki v Michael Redlicki | 7-6,6-2 |
| Challenger Winnetka Qual | 2018/07/07 18:05 | Alexander Knight v Michael Redlicki | 3-6,2-6 |
| ITF USA F17 | 2018/06/26 22:20 | Michael Redlicki v Jenson Brooksby | 6-2,6-3 |
| ITF USA F15 | 2018/06/24 14:00 | Tommy Paul v Michael Redlicki | 3-6,6-3,1-6 |
| ITF USA F15 | 2018/06/23 16:20 | Michael Redlicki v Skander Mansouri | 4-6,6-3,7-5 |
| 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 Canada F3 | 2018/06/24 16:00 | Juan Carlos Aguilar v Paul Oosterbaan | 5-7,6-3,5-7 |
| ITF Canada F3 | 2018/06/22 17:00 | Paul Oosterbaan v Samuel Monette | 2-6,6-4,6-4 |
| ITF Canada F3 | 2018/06/21 19:45 | Gerardo L Villasenor v Paul Oosterbaan | 6-7,6-7 |