| 1. Round | 02/03/2019 | Houston Dynamo | - | Real Salt Lake | 1:1 |  |
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| 1. Round | 16/03/2019 | Houston Dynamo | - | Vancouver Whitecaps | 3:2 | ||||
| 3. Round | 26/05/2019 | Minnesota United FC | - | Houston Dynamo | 1:0 | ||||
| 4. Round | 23/06/2019 | Portland Timbers | - | Houston Dynamo | 4:0 | ||||
| 4. Round | 27/06/2019 | San Jose Earthquakes | - | Houston Dynamo | 2:0 | ||||
| 4. Round | 30/06/2019 | New England Revolution | - | Houston Dynamo | 2:1 | ||||
| 5. Round | 07/07/2019 | FC Cincinnati | - | Houston Dynamo | 3:2 | ||||
| 5. Round | 18/07/2019 | Atlanta United FC | - | Houston Dynamo | 5:0 | ||||
| 5. Round | 21/07/2019 | Toronto FC | - | Houston Dynamo | 1:3 | ||||
| 5. Round | 28/07/2019 | Houston Dynamo | - | Seattle Sounders | 0:1 | ||||
| 7. Round | 01/09/2019 | Sporting Kansas City | - | Houston Dynamo | 1:0 | ||||
| 7. Round | 12/09/2019 | Houston Dynamo | - | Minnesota United FC | 2:0 |
USA