| | | |
| March 1, 2026 | W | San Jose Earthquakes II 1 at Portland Timbers 2 2 | Final |
| March 8, 2026 | T | Vancouver Whitecaps FC 2 0 at Portland Timbers 2 0 | Final (PK 6-7) |
| March 15, 2026 | L | Portland Timbers 2 0 at Houston Dynamo 2 5 | Final |
| March 23, 2026 | T | Ventura County FC 0 at Portland Timbers 2 0 | Final (PK 8-7) |
| April 15, 2026 | W | Portland Timbers 2 1 at LAFC2 0 | Final |
| April 19, 2026 | T | North Texas SC 2 at Portland Timbers 2 2 | Final (PK 5-3) |
| May 3, 2026 | W | Portland Timbers 2 3 at Real Monarchs 0 | Final |
| May 10, 2026 | T | Ventura County FC 3 at Portland Timbers 2 3 | Final (PK 7-6) |
| May 13, 2026 | W | Minnesota United FC 2 1 at Portland Timbers 2 2 | Final |
| May 17, 2026 | W | Portland Timbers 2 1 at San Jose Earthquakes II 0 | Final |
| May 24, 2026 | L | Houston Dynamo 2 3 at Portland Timbers 2 0 | Final |
| May 31, 2026 | W | Tacoma Defiance 0 at Portland Timbers 2 1 | Final |
| June 5, 2026 | | Portland Timbers 2 at Vancouver Whitecaps FC 2 | 9:00 p.m. |
| June 13, 2026 | | Portland Timbers 2 at Real Monarchs | 5:30 p.m. |
| June 20, 2026 | | Portland Timbers 2 at Colorado Rapids 2 | 8:00 p.m. |
| June 27, 2026 | | San Jose Earthquakes II at Portland Timbers 2 | 4:00 p.m. |
| July 5, 2026 | | Portland Timbers 2 at Tacoma Defiance | 10:00 p.m. |
| July 11, 2026 | | Portland Timbers 2 at LAFC2 | 10:00 p.m. |
| July 18, 2026 | | Portland Timbers 2 at St. Louis City SC 2 | 7:00 p.m. |
| July 26, 2026 | | Real Monarchs at Portland Timbers 2 | 4:00 p.m. |
| July 31, 2026 | | Portland Timbers 2 at Minnesota United FC 2 | 8:00 p.m. |
| August 8, 2026 | | LAFC2 at Portland Timbers 2 | 4:00 p.m. |
| August 15, 2026 | | Portland Timbers 2 at North Texas SC | 8:45 p.m. |
| August 23, 2026 | | Portland Timbers 2 at Ventura County FC | 7:00 p.m. |
| August 30, 2026 | | Austin FC II at Portland Timbers 2 | 4:00 p.m. |
| September 7, 2026 | | Vancouver Whitecaps FC 2 at Portland Timbers 2 | 4:00 p.m. |
| September 14, 2026 | | St. Louis City SC 2 at Portland Timbers 2 | 4:00 p.m. |
| September 20, 2026 | | Portland Timbers 2 at Tacoma Defiance | 5:00 p.m. |
Portland Timbers 2 Schedule
