On March 20, 2009, Major League Soccer commissioner Don Garber announced an expansion team had been granted to the Portland area and would retain the Timbers name.

In their inaugural season, the Timbers went to the championship game Soccer Bowl but lost to the Tampa Bay Rowdies 2–0.

Many of these Timbers continued to live in the area after their playing careers and helped establish the soccer as a vital local sport.

However, many exciting moments went along with the 2005 season, including a 6–1 thumping of the Atlanta Silverbacks on September 8, 2005; Portland being the only team to give the Montreal Impact a home loss, and Timbers players Scot Thompson, Hugo Alcaraz-Cuellar, and Dan Antoniuk winning league awards.

They enjoyed successful friendlies against Preston North End (2–1), Club Necaxa (1–0) and Toronto FC (4–1) while drawing even with the A.C. Milan Primavera squad (1–1) and winning on penalties, and went unbeaten at home during the regular season.

The team finished dead last with a 7–13–10 record, scored a league worst 26 goals, while conceding 33.

However, the 2008 Portland Timbers attendance grew 25.5% averaging 8,567 spectators (second in the USL-1 behind Montreal Impact), and Cameron Knowles won an All-League Second Team spot.

They went unbeaten for a USL-1 record 24 matches in a row, which started following a 1–0 loss to Vancouver in the first game of the season,[4] and ended with a Sep 3 defeat to Rochester Rhinos at PGE Park.

[5] They finished their season at the top of the table (16-4-10 58 points) winning The Commissioner's Cup and a first round bye in the playoffs.

[6] The Timbers were eliminated from the playoffs in their first two games (1–2, 3–3) on goal aggregate to Cascadia rival Vancouver Whitecaps.

There are many other groups that occupy the North End (Woodshed) of Providence Park, some who are a part of the Timbers Army, and some who are not.

Portland Timbers have rivalries with their Pacific Northwest opponents Seattle Sounders and Vancouver Whitecaps.

His final farewell was a game played against Puerto Rico Islanders on April 17, 2008, the Timbers home opener, which was won 1–0.