All countries
| Ventura County | Portland Timbers 2 | details | 24.08.2026 03:00 | ||||
| North Texas | Portland Timbers 2 | 0:3 (0:1, 0:2) | details | 16.08.2026 | ||||
| Portland Timbers 2 | Los Angeles FC 2 | 1:0 AfP (0:0, 0:0, 8:7) | details | 08.08.2026 | ||||
| Minnesota 2 | Portland Timbers 2 | 1:2 (1:1, 0:1) | details | 01.08.2026 | ||||
| Portland Timbers 2 | Real Monarchs | 1:0 (0:0, 1:0) | details | 26.07.2026 | ||||
| St. Louis City 2 | Portland Timbers 2 | 1:2 (0:0, 1:2) | details | 19.07.2026 | ||||
| Ventura County | Portland Timbers 2 | details | 24.08.2026 03:00 | ||||
| Portland Timbers 2 | Austin FC II | details | 30.08.2026 21:00 | ||||
| Portland Timbers 2 | Vancouver Whitecaps 2 | details | 07.09.2026 21:00 | ||||
| Portland Timbers 2 | St. Louis City 2 | details | 14.09.2026 21:00 | ||||