| 2. Round | 15/04/2018 | Louisville City FC | - | Richmond Kickers | 2:1 | ||||
| 5. Round | 22/07/2018 | Richmond Kickers | - | Atlanta United II | 1:1 |  |
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| 5. Round | 29/07/2018 | Charleston Battery | - | Richmond Kickers | 3:0 | ||||
| 6. Round | 05/08/2018 | Richmond Kickers | - | Bethlehem Steel FC | 0:3 | ||||
| 6. Round | 13/08/2018 | Toronto FC 2 | - | Richmond Kickers | 1:0 | ||||
| 6. Round | 26/08/2018 | Richmond Kickers | - | Louisville City FC | 0:6 | ||||
| 6. Round | 29/08/2018 | Nashville SC | - | Richmond Kickers | 4:0 | ||||
| 7. Round | 02/09/2018 | Indy Eleven | - | Richmond Kickers | 1:1 | ||||
| 7. Round | 09/09/2018 | Charlotte Independence | - | Richmond Kickers | 2:1 | ||||
| 7. Round | 16/09/2018 | Richmond Kickers | - | Ottawa Fury | 0:2 | ||||
| 7. Round | 23/09/2018 | Tampa Bay Rowdies | - | Richmond Kickers | 3:0 | ||||
| 7. Round | 27/09/2018 | Richmond Kickers | - | FC Cincinnati | 1:4 | ||||
| 7. Round | 30/09/2018 | North Carolina FC | - | Richmond Kickers | 3:2 | |
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| 8. Round | 07/10/2018 | Richmond Kickers | - | Nashville SC | 0:3 | |
USA