| 1. Round | 14/04/2019 | NC Courage [Women] | - | Chicago Red Stars [Women] | 1:1 | ||||
| 1. Round | 20/04/2019 | Chicago Red Stars [Women] | - | Portland Thorns [Women] | 4:4 | ||||
| 1. Round | 28/04/2019 | Chicago Red Stars [Women] | - | Reign FC [Women] | 3:0 | ||||
| 4. Round | 21/07/2019 | Chicago Red Stars [Women] | - | NC Courage [Women] | 2:1 | ||||
| 4. Round | 28/07/2019 | Reign FC [Women] | - | Chicago Red Stars [Women] | 0:4 | ||||
| 5. Round | 11/08/2019 | Washington Spirit [Women] | - | Chicago Red Stars [Women] | 0:1 | ||||
| 5. Round | 22/08/2019 | Chicago Red Stars [Women] | - | Orlando Pride [Women] | 1:2 |  |
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| 5. Round | 25/08/2019 | Portland Thorns [Women] | - | Chicago Red Stars [Women] | 3:0 | ||||
| 6. Round | 08/09/2019 | Chicago Red Stars [Women] | - | Houston Dash [Women] | 3:0 | ||||
| 6. Round | 15/09/2019 | Sky Blue FC [Women] | - | Chicago Red Stars [Women] | 0:3 | ||||
| 6. Round | 22/09/2019 | Chicago Red Stars [Women] | - | Washington Spirit [Women] | 3:1 | ||||
| 6. Round | 29/09/2019 | Chicago Red Stars [Women] | - | Utah Royals FC [Women] | 2:1 |
USA