The first competitive game of the 2009 season was played on April 25 at Swangard Stadium in Burnaby, BC versus Vancouver Whitecaps FC which the Timbers lost 1–0.

Following that loss the Timbers went on a 24-game unbeaten streak in the league on their way to securing the Commissioner's Cup for finishing the regular season atop the table.

In a hard-fought, two-legged series, Vancouver Whitecaps FC knocked Portland out of the playoffs in the semifinals by an aggregate score of 5–4.

In the U.S. Open Cup the Timbers hosted Seattle Sounders FC of Major League Soccer in the third round but were eliminated by their bitter rivals 2–1 in front of 16,382 spectators at PGE Park in Portland, Oregon.

Commissioner's Cup, bye to semifinal round of playoffs Quarterfinal round of playoffs † Austin deducted two points for fielding an ineligible player on July 25, 2009[1] Last updated: April 26, 2010 Source: uslsoccer.com Pld = Matches played; Pts = Points; W = Matches won; T = Matches tied; L = Matches lost; GF = Goals for; GA = Goals against; GD = Goal difference Teams were re-seeded for semifinal matchups Second Round winners advance to play one of 8 MLS clubs in 16-team knockout tournament Home teams listed on top of bracket