| | | |
| February 21, 2026 | W | Columbus Crew SC 2 at Portland Timbers 3 | Final |
| February 28, 2026 | L | Portland Timbers 0 at Colorado Rapids 2 | Final |
| March 7, 2026 | L | Vancouver Whitecaps FC 4 at Portland Timbers 1 | Final |
| March 14, 2026 | L | Portland Timbers 2 at Houston Dynamo FC 3 | Final |
| March 22, 2026 | T | LA Galaxy 1 at Portland Timbers 1 | Final |
| April 4, 2026 | L | Portland Timbers 2 at Vancouver Whitecaps FC 3 | Final |
| April 11, 2026 | W | Los Angeles FC 1 at Portland Timbers 2 | Final |
| April 18, 2026 | L | Portland Timbers 0 at Minnesota United FC 2 | Final |
| April 25, 2026 | W | Portland Timbers 2 at San Diego FC 1 | Final |
| May 2, 2026 | L | Portland Timbers 0 at Real Salt Lake 2 | Final |
| May 9, 2026 | W | Sporting Kansas City 0 at Portland Timbers 6 | Final |
| May 13, 2026 | T | Portland Timbers 2 at Club de Foot Montreal 2 | Final |
| May 17, 2026 | L | Portland Timbers 0 at Inter Miami CF 2 | Final |
| May 23, 2026 | L | San Jose Earthquakes 3 at Portland Timbers 1 | Final |
| July 16, 2026 | W | Portland Timbers 5 at Seattle Sounders FC 1 | Final |
| July 22, 2026 | T | FC Dallas 2 at Portland Timbers 2 | Final |
| July 25, 2026 | W | Real Salt Lake 1 at Portland Timbers 2 | Final |
| August 1, 2026 | W | Seattle Sounders FC 1 at Portland Timbers 2 | Final |
| August 16, 2026 | L | Portland Timbers 1 at Chicago Fire FC 2 | Final |
| August 19, 2026 | W | San Diego FC 1 at Portland Timbers 3 | Final |
| August 22, 2026 | T | Portland Timbers 1 at Los Angeles FC 1 | Final |
| August 29, 2026 | L | Austin FC 2 at Portland Timbers 1 | Final |
| September 5, 2026 | W | Minnesota United FC 4 at Portland Timbers 5 | Final |
| September 9, 2026 | T | St. Louis City SC 2 at Portland Timbers 2 | Final |
| September 12, 2026 | L | Portland Timbers 1 at FC Dallas 2 | Final |
| September 19, 2026 | L | Atlanta United FC 1 at Portland Timbers 0 | Final |
| September 26, 2026 | L | Portland Timbers 1 at San Jose Earthquakes 3 | Final |
| October 10, 2026 | T | Portland Timbers 3 at Sporting Kansas City 3 | Final |
| October 14, 2026 | L | Portland Timbers 0 at LA Galaxy 2 | Final |
| October 17, 2026 | | Colorado Rapids at Portland Timbers | 9:30 p.m. |
| October 24, 2026 | | Charlotte FC at Portland Timbers | 9:30 p.m. |
| October 28, 2026 | | Portland Timbers at St. Louis City SC | 7:30 p.m. |
| November 1, 2026 | | Houston Dynamo FC at Portland Timbers | 9:30 p.m. |
| November 7, 2026 | | Portland Timbers at Austin FC | 7:00 p.m. |
Portland Timbers Schedule
