2. Round | 22/04/2018 | Penn FC | - | Charleston Battery | 1:1 | ||||
2. Round | 24/04/2018 | Penn FC | - | Nashville SC | 0:0 | ||||
2. Round | 29/04/2018 | North Carolina FC | - | Penn FC | 3:0 | ||||
3. Round | 05/05/2018 | Penn FC | - | Tampa Bay Rowdies | 3:0 | ||||
3. Round | 07/05/2018 | Penn FC | - | Ottawa Fury | 0:1 | ||||
3. Round | 09/05/2018 | Toronto FC 2 | - | Penn FC | 0:1 | ||||
3. Round | 27/05/2018 | Pittsburgh Riverhounds | - | Penn FC | 0:0 | ||||
4. Round | 03/06/2018 | Nashville SC | - | Penn FC | 3:1 | ||||
4. Round | 10/06/2018 | Penn FC | - | Toronto FC 2 | 3:2 | ||||
4. Round | 13/06/2018 | Penn FC | - | Richmond Kickers | 2:1 | ||||
4. Round | 17/06/2018 | Louisville City FC | - | Penn FC | 3:3 | ||||
4. Round | 23/06/2018 | Tampa Bay Rowdies | - | Penn FC | 1:2 | ||||
4. Round | 01/07/2018 | Indy Eleven | - | Penn FC | 1:1 | ||||
5. Round | 07/07/2018 | Penn FC | - | Bethlehem Steel FC | 3:2 | ||||
5. Round | 10/07/2018 | Penn FC | - | Richmond Kickers | 1:2 |