| 1. Round | 23/03/2019 | Philadelphia Union | - | Columbus Crew | 3:0 | ||||
| 2. Round | 21/04/2019 | Columbus Crew | - | Portland Timbers | 1:3 | ||||
| 3. Round | 05/05/2019 | D.C. United | - | Columbus Crew | 3:1 | ||||
| 4. Round | 23/06/2019 | Columbus Crew | - | Sporting Kansas City | 0:1 | ||||
| 4. Round | 30/06/2019 | Columbus Crew | - | Orlando City | 0:2 | ||||
| 5. Round | 04/07/2019 | Real Salt Lake | - | Columbus Crew | 1:0 | ||||
| 5. Round | 07/07/2019 | Columbus Crew | - | Seattle Sounders | 1:2 |
USA