1. Round | 24/03/2018 | Charleston Battery | - | Penn FC | 1:0 | ||||
1. Round | 01/04/2018 | Pittsburgh Riverhounds | - | Penn FC | 0:0 | ||||
2. Round | 24/04/2018 | Penn FC | - | Nashville SC | 0:0 | ||||
3. Round | 09/05/2018 | Toronto FC 2 | - | Penn FC | 0:1 | ||||
3. Round | 27/05/2018 | Pittsburgh Riverhounds | - | Penn FC | 0:0 | ||||
5. Round | 29/07/2018 | Charlotte Independence | - | Penn FC | 1:1 | ||||
6. Round | 26/08/2018 | Ottawa Fury | - | Penn FC | 0:2 | ||||
7. Round | 19/09/2018 | Penn FC | - | Louisville City FC | 0:3 |