| 1. Round | 06/03/2016 | Chicago Fire | - | New York City FC | 3:4 |  |
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| 1. Round | 12/03/2016 | Orlando City | - | Chicago Fire | 1:1 | ||||
| 1. Round | 19/03/2016 | Chicago Fire | - | Columbus Crew | 0:0 | ||||
| 2. Round | 02/04/2016 | Chicago Fire | - | Philadelphia Union | 1:0 | |
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| 2. Round | 11/04/2016 | New York City FC | - | Chicago Fire | 0:0 | ||||
| 2. Round | 16/04/2016 | Chicago Fire | - | Impact de Montréal | 1:2 | |
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| 2. Round | 30/04/2016 | Chicago Fire | - | D.C. United | 1:1 |  |
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| 3. Round | 12/05/2016 | Vancouver Whitecaps | - | Chicago Fire | 2:1 | |
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| 3. Round | 15/05/2016 | New England Revolution | - | Chicago Fire | 2:0 | ||||
| 3. Round | 19/05/2016 | New York RB | - | Chicago Fire | 1:0 | ||||
| 3. Round | 21/05/2016 | Chicago Fire | - | Houston Dynamo | 1:0 | |
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| 3. Round | 29/05/2016 | Chicago Fire | - | Portland Timbers | 1:1 | ||||
| 4. Round | 19/06/2016 | Colorado Rapids | - | Chicago Fire | 2:1 | ||||
| 4. Round | 23/06/2016 | Philadelphia Union | - | Chicago Fire | 4:3 | ||||
| 5. Round | 02/07/2016 | Chicago Fire | - | San Jose Earthquakes | 1:0 | ||||
| 5. Round | 10/07/2016 | Toronto FC | - | Chicago Fire | 1:0 | ||||
| 5. Round | 17/07/2016 | FC Dallas | - | Chicago Fire | 3:1 | ||||
| 5. Round | 24/07/2016 | New England Revolution | - | Chicago Fire | 1:0 |
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