| 1. Round | 26/02/2023 | Philadelphia Union | - | Columbus Crew | 4:1 | ||||
| 2. Round | 05/03/2023 | Columbus Crew | - | D.C. United | 2:0 | ||||
| 2. Round | 12/03/2023 | Toronto FC | - | Columbus Crew | 1:1 | ||||
| 7. Round | 27/08/2023 | Columbus Crew | - | Toronto FC | 2:0 | ||||
| 8. Round | 03/09/2023 | CF Montréal | - | Columbus Crew | 2:4 | ||||
| 8. Round | 17/09/2023 | Orlando City | - | Columbus Crew | 4:3 | ||||
| 8. Round | 21/09/2023 | Columbus Crew | - | Chicago Fire | 3:0 | ||||
| 8. Round | 01/10/2023 | Columbus Crew | - | Philadelphia Union | 1:1 | ||||
| 9. Round | 08/10/2023 | Atlanta United FC | - | Columbus Crew | 1:1 |
Trinidad & Tobago
