| 1. Round | 03/07/2016 | Minnesota United FC | - | Carolina RailHawks | 5:1 | ||||
| 1. Round | 10/07/2016 | Indy Eleven | - | Minnesota United FC | 1:0 |  |
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| 1. Round | 17/07/2016 | Minnesota United FC | - | Indy Eleven | 2:0 | ||||
| 1. Round | 24/07/2016 | Minnesota United FC | - | Fort Lauderdale Strikers | 3:1 | ||||
| 2. Round | 04/08/2016 | Minnesota United FC | - | Puerto Rico FC | 1:1 | ||||
| 2. Round | 14/08/2016 | FC Edmonton | - | Minnesota United FC | 1:0 | ||||
| 2. Round | 18/08/2016 | Minnesota United FC | - | Tampa Bay Rowdies | 2:0 | ||||
| 2. Round | 20/08/2016 | Jacksonville Armada | - | Minnesota United FC | 0:0 | ||||
| 2. Round | 28/08/2016 | Miami FC | - | Minnesota United FC | 1:1 | ||||
| 2. Round | 01/09/2016 | Fort Lauderdale Strikers | - | Minnesota United FC | 0:0 | ||||
| 3. Round | 04/09/2016 | Minnesota United FC | - | Rayo OKC | 1:0 | |
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| 3. Round | 11/09/2016 | New York Cosmos | - | Minnesota United FC | 1:0 | ||||
| 3. Round | 18/09/2016 | Minnesota United FC | - | Ottawa Fury | 2:3 | ||||
| 3. Round | 25/09/2016 | Ottawa Fury | - | Minnesota United FC | 3:1 | ||||
| 4. Round | 02/10/2016 | Minnesota United FC | - | Jacksonville Armada | 0:1 | |
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| 4. Round | 23/10/2016 | Carolina RailHawks | - | Minnesota United FC | 1:0 | |
USA