| | | |
| February 23, 2025 | L | Vancouver Whitecaps FC 4 at Portland Timbers 1 | Final |
| March 1, 2025 | W | Austin FC 0 at Portland Timbers 1 | Final |
| March 8, 2025 | L | Portland Timbers 0 at Nashville SC 2 | Final |
| March 16, 2025 | T | LA Galaxy 1 at Portland Timbers 1 | Final |
| March 22, 2025 | W | Portland Timbers 3 at Colorado Rapids 0 | Final |
| March 30, 2025 | W | Houston Dynamo FC 1 at Portland Timbers 3 | Final |
| April 5, 2025 | T | Portland Timbers 0 at Austin FC 0 | Final |
| April 13, 2025 | W | Portland Timbers 4 at Sporting Kansas City 2 | Final |
| April 19, 2025 | T | Los Angeles FC 3 at Portland Timbers 3 | Final |
| April 27, 2025 | W | Portland Timbers 4 at LA Galaxy 2 | Final |
| May 3, 2025 | L | Portland Timbers 1 at San Jose Earthquakes 4 | Final |
| May 10, 2025 | W | Sporting Kansas City 0 at Portland Timbers 1 | Final |
| May 14, 2025 | T | Portland Timbers 0 at Real Salt Lake 0 | Final |
| May 17, 2025 | T | Seattle Sounders FC 1 at Portland Timbers 1 | Final |
| May 24, 2025 | L | Portland Timbers 0 at Orlando City SC 1 | Final |
| May 28, 2025 | W | Colorado Rapids 1 at Portland Timbers 2 | Final |
| June 8, 2025 | W | St. Louis City SC 1 at Portland Timbers 2 | Final |
| June 13, 2025 | T | San Jose Earthquakes 1 at Portland Timbers 1 | Final |
| June 28, 2025 | L | Portland Timbers 0 at Toronto FC 3 | Final |
| July 5, 2025 | W | New England Revolution 1 at Portland Timbers 2 | Final |
| July 13, 2025 | L | Portland Timbers 1 at St. Louis City SC 2 | Final |
| July 16, 2025 | L | Real Salt Lake 1 at Portland Timbers 0 | Final |
| July 19, 2025 | T | Minnesota United FC 1 at Portland Timbers 1 | Final |
| July 25, 2025 | W | Portland Timbers 1 at Los Angeles FC 0 | Final |
| August 9, 2025 | L | Portland Timbers 0 at FC Dallas 2 | Final |
| August 16, 2025 | L | FC Cincinnati 3 at Portland Timbers 2 | Final |
| August 23, 2025 | T | Portland Timbers 0 at San Diego FC 0 | Final |
| August 30, 2025 | T | Portland Timbers 1 at Minnesota United FC 1 | Final |
| September 13, 2025 | W | New York Red Bulls 1 at Portland Timbers 2 | Final |
| September 20, 2025 | L | Portland Timbers 0 at Houston Dynamo FC 1 | Final |
| September 24, 2025 | T | Portland Timbers 1 at Vancouver Whitecaps FC 1 | Final |
| September 27, 2025 | T | FC Dallas 2 at Portland Timbers 2 | Final |
| October 4, 2025 | L | Portland Timbers 0 at Seattle Sounders FC 1 | Final |
| October 18, 2025 | L | San Diego FC 4 at Portland Timbers 0 | Final |
| October 22, 2025 | W | Real Salt Lake 1 at Portland Timbers 3 (Playoff) | Final |
| October 26, 2025 | L | Portland Timbers 1 at San Diego FC 2 (Playoff Gm. 1) | Final |
| November 1, 2025 | T | San Diego FC 2 at Portland Timbers 2 (Playoff Gm. 2) | Final (PK 2-3) |
| November 9, 2025 | L | Portland Timbers 0 at San Diego FC 4 (Playoff Gm. 3) | Final |
Portland Timbers Schedule
