| 1. Round | 03/04/2016 | New York Cosmos | - | Ottawa Fury | 3:0 |  |
|||
| 2. Round | 10/04/2016 | New York Cosmos | - | Jacksonville Armada | 2:0 |  |
|
||
| 3. Round | 17/04/2016 | Indy Eleven | - | New York Cosmos | 2:1 | ||||
| 4. Round | 24/04/2016 | Minnesota United FC | - | New York Cosmos | 1:0 | ||||
| 5. Round | 01/05/2016 | New York Cosmos | - | Carolina RailHawks | 1:0 | ||||
| 6. Round | 08/05/2016 | Miami FC | - | New York Cosmos | 0:3 | |
|
||
| 7. Round | 15/05/2016 | FC Edmonton | - | New York Cosmos | 2:1 | ||||
| 9. Round | 29/05/2016 | New York Cosmos | - | Rayo OKC | 1:0 | ||||
| 10. Round | 05/06/2016 | Fort Lauderdale Strikers | - | New York Cosmos | 2:1 |
Costa Rica