1. Round | 03/03/2019 | Los Angeles Galaxy | - | Chicago Fire | 2:1 | ||||
2. Round | 13/04/2019 | Chicago Fire | - | Vancouver Whitecaps | 1:1 | ||||
2. Round | 28/04/2019 | Impact de Montréal | - | Chicago Fire | 1:0 | ||||
3. Round | 09/05/2019 | Chicago Fire | - | New England Revolution | 5:0 | ||||
3. Round | 25/05/2019 | Chicago Fire | - | New York City FC | 1:1 |