Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 24.03.2019 |  | Matchday 1 | Portland Timbers 2 - Las Vegas Lights FC | - | 3:1 | 2.124 |
| 14.04.2019 | | Matchday 2 | Portland Timbers 2 - Sacramento Rep | - | 1:0 | 1.116 |
| 21.04.2019 | | Matchday 2 | Portland Timbers 2 - Colorado Springs Switchbacks | - | 2:2 | 1.822 |
| 01.05.2019 | | Matchday 3 | Portland Timbers 2 - RGV FC | - | 1:2 | 1.120 |
| 07.07.2019 | | Matchday 5 | Portland Timbers 2 - FC Tulsa | - Tul | 1:1 | 1.986 |