| 1. Round | 24/03/2018 | Richmond Kickers | - | Indy Eleven | 0:1 | ||||
| 1. Round | 31/03/2018 | Richmond Kickers | - | North Carolina FC | 2:1 | ||||
| 2. Round | 07/04/2018 | Richmond Kickers | - | New York RB II | 1:1 | ||||
| 3. Round | 13/05/2018 | Richmond Kickers | - | Tampa Bay Rowdies | 1:0 | ||||
| 5. Round | 14/07/2018 | New York RB II | - | Richmond Kickers | 5:1 | ||||
| 5. Round | 22/07/2018 | Richmond Kickers | - | Atlanta United II | 1:1 | ||||
| 6. Round | 02/08/2018 | Pittsburgh Riverhounds | - | Richmond Kickers | 3:0 |  |
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| 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 | 16/09/2018 | Richmond Kickers | - | Ottawa Fury | 0:2 |
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