| 4. Round | 28/09/2020 | Toronto FC | - | Columbus Crew | 3:1 |  |
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| 5. Round | 04/10/2020 | FC Dallas | - | Columbus Crew | 2:2 | ||||
| 5. Round | 08/10/2020 | Columbus Crew | - | Impact de Montréal | 1:2 | ||||
| 5. Round | 15/10/2020 | FC Cincinnati | - | Columbus Crew | 2:1 | |
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| 5. Round | 18/10/2020 | Columbus Crew | - | New York City FC | 3:1 | ||||
| 5. Round | 25/10/2020 | Houston Dynamo | - | Columbus Crew | 1:1 | |
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| 6. Round | 05/11/2020 | Orlando City | - | Columbus Crew | 2:1 | ||||
| 6. Round | 08/11/2020 | Columbus Crew | - | Atlanta United FC | 2:1 |
USA
Canada