The club's first game was played at Dick's Sporting Goods Park versus Colorado Rapids on March 19, which the Timbers lost 3–1.

The first MLS match in Portland was on April 14 when the Timbers bested the Chicago Fire by a scoreline of 4–2 in front of a sold-out crowd of 18,627 at newly renovated Jeld-Wen Field.

The Timbers came into their first MLS game nursing injuries to several players including expected starters Darlington Nagbe, Sal Zizzo and Troy Perkins as well as Bright Dike and Eddie Johnson.

[1] The defending champions Colorado Rapids took the field with the same 11 players which had started MLS Cup 2010 and dealt the Timbers an early blow with an 8th-minute goal by Jeff Larentowicz.

[3] Prior to the March 26 game versus Toronto FC, it was announced that defender Mamadou Danso had been called up for Gambia and would miss the match.

[7] Unlike previous years when second division Portland sides were often guaranteed a spot in the U.S. Open Cup, the Timbers would have to defeat three other MLS teams in a qualification tournament in order to join the competition.

The Timbers began their campaign to qualify for the 2011 U.S. Open Cup on March 29 as the team played their first game in Portland versus Chivas USA.

It took nearly the entire second half for the Timbers to capitalize on the man advantage as substitute Jack Jewsbury finally gave Portland the lead with a long-range strike in the 84th minute.

Captain for the night, Eric Brunner, sealed a first-ever competitive win for the Timbers with a headed goal two minutes later as Portland won 2–0 to advance to the semifinals of the qualification tournament versus the San Jose Earthquakes.

[9] Hoping to build on their positive result in Portland, the Timbers started the league game against the New England Revolution with the same 11 players which were on the field at the conclusion of the U.S. Open Cup qualification win versus Chivas USA.

[12] The next day it was announced that the Timbers would host the U.S. Open Cup qualification semifinal match vs. San Jose Earthquakes at Jeld-Wen Field on May 3.

San Jose originally won hosting rights for the game through a preseason coin toss but was unable to secure a venue in time.

The 25-year-old Colombian midfielder, who was a childhood friend and recent teammate of Jorge Perlaza at Deportes Tolima, was expected to join the Timbers after acquiring his P-1 visa.

Prior to kickoff, the Timbers Army sang the national anthem en masse while accompanied by fireworks and subsequently revealed a large tifo display celebrating the city of Portland.

[16] A boisterous sell-out crowd of 18,627 watched as Jorge Perlaza scored his first goal for the Timbers in the 29th minute to give Portland their first lead of the season.

The dream start to Portland's home opener continued just after halftime when Perlaza pounced on a spilled rebound by Fire goalkeeper Sean Johnson to give the Timbers a 3–0 lead.

The Timbers used their other two expansion picks to select the rights of players leaving MLS: forward Robbie Findley and defender Jonathan Bornstein.

"We get the international slot for a year and ultimately, through the deals, we're banking some allocation money," said Portland general manager and technical director Gavin Wilkinson.

"So, the way we walk out of it, at the end of that, we're lucky to get the player we absolutely loved [Darlington Nagbe, chosen 2nd overall by Portland] and an international spot, which is needed in the way that we're trying to build this squad.

On January 17, the club entered the international transfer market and acquired forward Kenny Cooper from Bundesliga 2 side 1860 Munich for an undisclosed fee.

[25] During the first preseason game against Ventura County Fusion on February 4, first round draft pick Darlington Nagbe scored in the second half to earn Portland a 1–1 draw.

Newly acquired Los Angeles midfielder Miguel Pedro López was shown a red card in the first half but the Galaxy were allowed to replace him due to the nature of the match.

[34] On March 1, the Timbers sent allocation money to Sporting Kansas City in exchange for midfielder Jack Jewsbury just before leaving for Tukwila, Washington to attend the 2011 Cascadia Summit.

[36] The first match of the Cascadia Summit saw the Timbers defeat hosts Seattle Sounders FC 2–0 off of goals by trialist Jorge Perlaza and Kenny Cooper.

Midfielder Ryan Pore scored early in the first half but the Whitecaps equalized before halftime thanks to an own goal from defender David Horst.

[39] Portland officially signed trialist Jorge Perlaza on March 7 after clearing up a complicated contract situation with his previous club, Deportes Tolima.

[41] The Timbers played their final preseason game on March 12 versus fellow Western Conference side San Jose Earthquakes at Buck Shaw Stadium in Santa Clara, California.

San Jose defender Chris Leitch was sent off late in the game but, due to it being a preseason training match, the Earthquakes were allowed to replace him.

[43] Although it had been widely reported in Uganda for several weeks, the Timbers officially announced the signing of forward Brian Umony on a year-long loan from South African side Tuks FC on March 16.

This list shows players who have played for the team in official 2011 MLS Reserve Division games, but are not part of the senior roster.