| 1. Round | 10/03/2019 | Los Angeles Galaxy II | - | Colorado Springs Switchbacks | 1:4 | ||||
| 1. Round | 17/03/2019 | Colorado Springs Switchbacks | - | Sacramento Republic | 0:1 | ||||
| 1. Round | 24/03/2019 | Colorado Springs Switchbacks | - | San Antonio FC | 1:0 | ||||
| 1. Round | 31/03/2019 | Phoenix Rising | - | Colorado Springs Switchbacks | 2:2 | ||||
| 2. Round | 07/04/2019 | Orange County SC | - | Colorado Springs Switchbacks | 2:0 | ||||
| 2. Round | 14/04/2019 | Colorado Springs Switchbacks | - | Reno 1868 FC | 0:2 | ||||
| 2. Round | 21/04/2019 | Portland Timbers 2 | - | Colorado Springs Switchbacks | 2:2 | ||||
| 2. Round | 25/04/2019 | Tulsa Roughnecks | - | Colorado Springs Switchbacks | 2:0 | ||||
| 3. Round | 05/05/2019 | Colorado Springs Switchbacks | - | El Paso Locomotive | 0:2 | ||||
| 3. Round | 12/05/2019 | Las Vegas Lights FC | - | Colorado Springs Switchbacks | 3:0 | ||||
| 3. Round | 19/05/2019 | Colorado Springs Switchbacks | - | New Mexico United | 1:3 |  |
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| 3. Round | 26/05/2019 | OKC Energy FC | - | Colorado Springs Switchbacks | 1:0 | ||||
| 4. Round | 02/06/2019 | Colorado Springs Switchbacks | - | Fresno FC | 1:0 | |
USA