| | | |
| March 15, 2025 | L | Real Monarchs 3 at Portland Timbers 2 2 | Final |
| March 26, 2025 | T | The Town FC 1 at Portland Timbers 2 1 | Final (PK 3-4) |
| March 29, 2025 | T | Portland Timbers 2 1 at Vancouver Whitecaps FC 2 1 | Final (PK 4-5) |
| April 5, 2025 | L | North Texas SC 2 at Portland Timbers 2 1 | Final |
| April 13, 2025 | L | Colorado Rapids 2 2 at Portland Timbers 2 1 | Final |
| April 23, 2025 | W | Portland Timbers 2 3 at Ventura County FC 2 | Final |
| May 4, 2025 | L | Portland Timbers 2 0 at The Town FC 5 | Final |
| May 9, 2025 | W | Vancouver Whitecaps FC 2 0 at Portland Timbers 2 1 | Final |
| May 14, 2025 | W | LAFC2 0 at Portland Timbers 2 3 | Final |
| May 18, 2025 | W | Tacoma Defiance 1 at Portland Timbers 2 2 | Final |
| May 23, 2025 | L | Portland Timbers 2 3 at St. Louis City SC 2 6 | Final |
| May 28, 2025 | L | Portland Timbers 2 1 at Real Monarchs 4 | Final |
| June 11, 2025 | L | Ventura County FC 3 at Portland Timbers 2 2 | Final |
| June 20, 2025 | T | Austin FC II 1 at Portland Timbers 2 1 | Final (PK 5-4) |
| July 5, 2025 | W | Portland Timbers 2 4 at Sporting Kansas City II 0 | Final |
| July 13, 2025 | L | Portland Timbers 2 0 at LAFC2 1 | Final |
| July 18, 2025 | T | Minnesota United FC 2 1 at Portland Timbers 2 1 | Final (PK 3-5) |
| July 27, 2025 | W | Portland Timbers 2 2 at Tacoma Defiance 1 | Final |
| August 3, 2025 | L | Real Monarchs 2 at Portland Timbers 2 1 | Final |
| August 9, 2025 | | Portland Timbers 2 at Ventura County FC | 10:00 p.m. |
| August 20, 2025 | | Portland Timbers 2 at Colorado Rapids 2 | 8:00 p.m. |
| August 24, 2025 | | Tacoma Defiance at Portland Timbers 2 | 11:00 p.m. |
| August 31, 2025 | | Portland Timbers 2 at Vancouver Whitecaps FC 2 | 7:00 p.m. |
| September 7, 2025 | | Portland Timbers 2 at The Town FC | 8:00 p.m. |
| September 14, 2025 | | LAFC2 at Portland Timbers 2 | 4:00 p.m. |
| September 21, 2025 | | Portland Timbers 2 at Houston Dynamo 2 | 8:00 p.m. |
| September 26, 2025 | | Portland Timbers 2 at Austin FC II | 8:30 p.m. |
| October 5, 2025 | | St. Louis City SC 2 at Portland Timbers 2 | 4:00 p.m. |
Portland Timbers 2 Schedule
