| 1. Round | 14/04/2019 | NC Courage [Women] | - | Chicago Red Stars [Women] | 1:1 |  |
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| 1. Round | 20/04/2019 | Chicago Red Stars [Women] | - | Portland Thorns [Women] | 4:4 |  |
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| 1. Round | 28/04/2019 | Chicago Red Stars [Women] | - | Reign FC [Women] | 3:0 | ||||
| 2. Round | 04/05/2019 | Utah Royals FC [Women] | - | Chicago Red Stars [Women] | 1:0 | ||||
| 2. Round | 12/05/2019 | Chicago Red Stars [Women] | - | NC Courage [Women] | 3:1 | |
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| 2. Round | 19/05/2019 | Houston Dash [Women] | - | Chicago Red Stars [Women] | 1:2 | ||||
| 2. Round | 26/05/2019 | Chicago Red Stars [Women] | - | Washington Spirit [Women] | 0:2 | ||||
| 3. Round | 02/06/2019 | Portland Thorns [Women] | - | Chicago Red Stars [Women] | 3:0 | ||||
| 3. Round | 23/06/2019 | Chicago Red Stars [Women] | - | Reign FC [Women] | 0:1 | ||||
| 3. Round | 30/06/2019 | Orlando Pride [Women] | - | Chicago Red Stars [Women] | 2:3 | ||||
| 4. Round | 07/07/2019 | Chicago Red Stars [Women] | - | Sky Blue FC [Women] | 1:2 |
USA