| 4. Round | 02/06/2019 | Columbus Crew | - | New York City FC | 2:2 | ||||
| 6. Round | 11/08/2019 | Columbus Crew | - | FC Cincinnati | 2:2 | ||||
| 6. Round | 18/08/2019 | Columbus Crew | - | Toronto FC | 2:2 | ||||
| 6. Round | 22/08/2019 | New York City FC | - | Columbus Crew | 1:0 | ||||
| 6. Round | 25/08/2019 | FC Cincinnati | - | Columbus Crew | 1:3 |  |
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| 7. Round | 01/09/2019 | Columbus Crew | - | Chicago Fire | 1:1 | ||||
| 7. Round | 15/09/2019 | Atlanta United FC | - | Columbus Crew | 1:3 | ||||
| 7. Round | 21/09/2019 | Vancouver Whitecaps | - | Columbus Crew | 1:1 | ||||
| 7. Round | 29/09/2019 | Columbus Crew | - | Philadelphia Union | 2:0 | ||||
| 8. Round | 06/10/2019 | Toronto FC | - | Columbus Crew | 1:0 |
USA