| 6. Round | 14/08/2016 | Chicago Fire | - | Orlando City | 2:2 |  |
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| 6. Round | 21/08/2016 | Colorado Rapids | - | Orlando City | 0:0 | |
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| 6. Round | 29/08/2016 | Orlando City | - | New York City FC | 2:1 | ||||
| 7. Round | 08/09/2016 | Impact de Montréal | - | Orlando City | 1:4 | ||||
| 7. Round | 12/09/2016 | Los Angeles Galaxy | - | Orlando City | 4:2 | ||||
| 7. Round | 25/09/2016 | D.C. United | - | Orlando City | 4:1 | ||||
| 7. Round | 29/09/2016 | Toronto FC | - | Orlando City | 0:0 | ||||
| 8. Round | 02/10/2016 | Orlando City | - | Impact de Montréal | 0:1 | ||||
| 8. Round | 16/10/2016 | Philadelphia Union | - | Orlando City | 0:2 | |
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| 8. Round | 23/10/2016 | Orlando City | - | D.C. United | 4:2 |
Uruguay