| 1. Round | 03/04/2016 | Fort Lauderdale Strikers | - | Miami FC | 1:1 |  |
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| 3. Round | 17/04/2016 | Minnesota United FC | - | Fort Lauderdale Strikers | 3:0 | ||||
| 9. Round | 28/05/2016 | Ottawa Fury | - | Fort Lauderdale Strikers | 1:2 | ||||
| 10. Round | 05/06/2016 | Fort Lauderdale Strikers | - | New York Cosmos | 2:1 | ||||
| 11. Round | 12/06/2016 | FC Edmonton | - | Fort Lauderdale Strikers | 2:1 |
Trinidad & Tobago