| 3. Round | 06/05/2019 | Sporting Kansas City | - | Atlanta United FC | 0:3 | ||||
| 3. Round | 13/05/2019 | D.C. United | - | Sporting Kansas City | 1:0 | ||||
| 3. Round | 26/05/2019 | Sporting Kansas City | - | Seattle Sounders | 3:2 | ||||
| 4. Round | 02/06/2019 | Houston Dynamo | - | Sporting Kansas City | 1:1 | ||||
| 4. Round | 08/06/2019 | Toronto FC | - | Sporting Kansas City | 2:2 | ||||
| 6. Round | 15/08/2019 | Orlando City | - | Sporting Kansas City | 1:0 | ||||
| 6. Round | 18/08/2019 | Sporting Kansas City | - | San Jose Earthquakes | 2:1 |  |
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| 6. Round | 23/08/2019 | Sporting Kansas City | - | Minnesota United FC | 1:0 | ||||
| 7. Round | 01/09/2019 | Sporting Kansas City | - | Houston Dynamo | 1:0 | ||||
| 7. Round | 08/09/2019 | Portland Timbers | - | Sporting Kansas City | 2:1 | ||||
| 7. Round | 16/09/2019 | Los Angeles Galaxy | - | Sporting Kansas City | 7:2 |  |
USA