2. Round | 24/04/2018 | Penn FC | - | Nashville SC | 0:0 | ||||
3. Round | 07/05/2018 | Penn FC | - | Ottawa Fury | 0:1 | ||||
3. Round | 09/05/2018 | Toronto FC 2 | - | Penn FC | 0:1 | ||||
4. Round | 17/06/2018 | Louisville City FC | - | Penn FC | 3:3 | ||||
5. Round | 10/07/2018 | Penn FC | - | Richmond Kickers | 1:2 | ||||
7. Round | 23/09/2018 | Penn FC | - | FC Cincinnati | 1:2 | ||||
7. Round | 26/09/2018 | Penn FC | - | Pittsburgh Riverhounds | 0:2 | ||||
8. Round | 09/10/2018 | Penn FC | - | New York RB II | 1:3 |