| 1. Round | 18/03/2018 | Bethlehem Steel FC | - | Richmond Kickers | 4:1 | ||||
| 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 |  |
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| 3. Round | 06/05/2018 | Bethlehem Steel FC | - | Richmond Kickers | 3:1 | |
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| 3. Round | 13/05/2018 | Richmond Kickers | - | Tampa Bay Rowdies | 1:0 | ||||
| 3. Round | 27/05/2018 | Richmond Kickers | - | Charlotte Independence | 1:3 | ||||
| 4. Round | 03/06/2018 | Richmond Kickers | - | Pittsburgh Riverhounds | 1:2 | ||||
| 4. Round | 10/06/2018 | Richmond Kickers | - | Charleston Battery | 2:0 | ||||
| 4. Round | 13/06/2018 | Penn FC | - | Richmond Kickers | 2:1 | ||||
| 4. Round | 17/06/2018 | FC Cincinnati | - | Richmond Kickers | 4:0 | ||||
| 4. Round | 24/06/2018 | Richmond Kickers | - | Charlotte Independence | 1:1 | ||||
| 4. Round | 01/07/2018 | Richmond Kickers | - | North Carolina FC | 1:3 | ||||
| 5. Round | 10/07/2018 | Penn FC | - | Richmond Kickers | 1:2 | ||||
| 5. Round | 14/07/2018 | New York RB II | - | Richmond Kickers | 5:1 | |
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| 6. Round | 05/08/2018 | Richmond Kickers | - | Bethlehem Steel FC | 0:3 | ||||
| 6. Round | 19/08/2018 | Richmond Kickers | - | Penn FC | 3:2 |
USA