| 1. Round | 10/03/2019 | San Antonio FC | - | Phoenix Rising | 3:3 |  |
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| 1. Round | 17/03/2019 | Phoenix Rising | - | New Mexico United | 3:3 | |
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| 1. Round | 31/03/2019 | Phoenix Rising | - | Colorado Springs Switchbacks | 2:2 | ||||
| 2. Round | 07/04/2019 | Phoenix Rising | - | Fresno FC | 0:0 | ||||
| 2. Round | 14/04/2019 | El Paso Locomotive | - | Phoenix Rising | 0:2 | ||||
| 2. Round | 18/04/2019 | Austin Bold | - | Phoenix Rising | 1:0 | ||||
| 2. Round | 21/04/2019 | Phoenix Rising | - | Tacoma Defiance | 4:0 | |
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| 2. Round | 28/04/2019 | Sacramento Republic | - | Phoenix Rising | 0:0 | ||||
| 7. Round | 08/09/2019 | Phoenix Rising | - | San Antonio FC | 1:0 | ||||
| 7. Round | 12/09/2019 | Las Vegas Lights FC | - | Phoenix Rising | 0:1 | ||||
| 8. Round | 13/10/2019 | Phoenix Rising | - | Real Monarchs SLC | 1:2 | ||||
| 8. Round | 19/10/2019 | Phoenix Rising | - | OKC Energy FC | 3:1 |
Jamaica