| 1. Round | 24/07/2016 | Tampa Bay Rowdies | - | New York Cosmos | 2:2 |  |
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| 1. Round | 28/07/2016 | FC Edmonton | - | New York Cosmos | 2:1 | ||||
| 1. Round | 31/07/2016 | New York Cosmos | - | Puerto Rico FC | 3:0 | ||||
| 2. Round | 07/08/2016 | New York Cosmos | - | Rayo OKC | 1:1 | ||||
| 2. Round | 14/08/2016 | New York Cosmos | - | Tampa Bay Rowdies | 3:2 | |
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| 2. Round | 21/08/2016 | Puerto Rico FC | - | New York Cosmos | 1:2 | ||||
| 3. Round | 29/09/2016 | Carolina RailHawks | - | New York Cosmos | 0:2 | |
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| 4. Round | 23/10/2016 | New York Cosmos | - | Miami FC | 4:0 | ||||
| 4. Round | 30/10/2016 | Minnesota United FC | - | New York Cosmos | 0:1 |
Bolivia