| 2. Round | 21/04/2018 | New York RB | - | Chicago Fire | 1:2 |  |
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| 2. Round | 28/04/2018 | Toronto FC | - | Chicago Fire | 2:2 | ||||
| 3. Round | 06/05/2018 | Chicago Fire | - | Atlanta United FC | 1:2 | ||||
| 3. Round | 10/05/2018 | Chicago Fire | - | Impact de Montréal | 1:0 | |
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| 3. Round | 13/05/2018 | Columbus Crew | - | Chicago Fire | 3:0 | ||||
| 3. Round | 20/05/2018 | Chicago Fire | - | Houston Dynamo | 2:3 | |
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| 3. Round | 27/05/2018 | Orlando City | - | Chicago Fire | 1:2 |  |
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| 3. Round | 31/05/2018 | Philadelphia Union | - | Chicago Fire | 3:1 | ||||
| 4. Round | 03/06/2018 | Chicago Fire | - | San Jose Earthquakes | 2:1 | ||||
| 4. Round | 10/06/2018 | Chicago Fire | - | New England Revolution | 1:1 | ||||
| 5. Round | 01/07/2018 | Chicago Fire | - | New York City FC | 3:2 | ||||
| 5. Round | 15/07/2018 | FC Dallas | - | Chicago Fire | 3:1 | ||||
| 5. Round | 22/07/2018 | Chicago Fire | - | Toronto FC | 1:2 | ||||
| 5. Round | 29/07/2018 | Toronto FC | - | Chicago Fire | 3:0 | ||||
| 6. Round | 24/08/2018 | Chicago Fire | - | Columbus Crew | 1:1 |
England
Eritrea