| 3. Round | 20/06/2021 | Columbus Crew | - | Chicago Fire | 2:0 | ||||
| 3. Round | 24/06/2021 | Philadelphia Union | - | Columbus Crew | 1:0 | ||||
| 3. Round | 28/06/2021 | Austin FC | - | Columbus Crew | 0:0 | ||||
| 4. Round | 22/07/2021 | Columbus Crew | - | Nashville SC | 0:0 | ||||
| 4. Round | 24/07/2021 | Atlanta United FC | - | Columbus Crew | 0:1 | ||||
| 4. Round | 31/07/2021 | New York City FC | - | Columbus Crew | 4:1 | ||||
| 5. Round | 05/08/2021 | Columbus Crew | - | D.C. United | 2:4 |  |
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| 5. Round | 08/08/2021 | Columbus Crew | - | Atlanta United FC | 2:3 | ||||
| 5. Round | 15/08/2021 | Chicago Fire | - | Columbus Crew | 1:0 | ||||
| 5. Round | 19/08/2021 | New York RB | - | Columbus Crew | 1:0 | ||||
| 5. Round | 21/08/2021 | Columbus Crew | - | Seattle Sounders | 1:2 |
Trinidad & Tobago
