| 1. Round | 08/03/2020 | Sporting Kansas City 2 | - | Charlotte Independence | 1:2 | ||||
| 2. Round | 19/07/2020 | Indy Eleven | - | Sporting Kansas City 2 | 2:1 | ||||
| 2. Round | 26/07/2020 | Louisville City FC | - | Sporting Kansas City 2 | 1:0 | ||||
| 2. Round | 30/07/2020 | Louisville City FC | - | Sporting Kansas City 2 | 1:2 | ||||
| 3. Round | 02/08/2020 | Indy Eleven | - | Sporting Kansas City 2 | 0:1 | ||||
| 3. Round | 06/08/2020 | Saint Louis FC | - | Sporting Kansas City 2 | 1:1 |  |
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| 3. Round | 30/08/2020 | FC Tulsa | - | Sporting Kansas City 2 | 1:2 | ||||
| 4. Round | 05/09/2020 | Saint Louis FC | - | Sporting Kansas City 2 | 3:2 | ||||
| 4. Round | 10/09/2020 | Indy Eleven | - | Sporting Kansas City 2 | 2:1 | ||||
| 4. Round | 20/09/2020 | Saint Louis FC | - | Sporting Kansas City 2 | 3:2 | ||||
| 4. Round | 23/09/2020 | Austin Bold | - | Sporting Kansas City 2 | 4:0 |
Congo