Although not taking part in the tryouts, Haitian national team midfielder James Marcelin[6] and Canadian defender Ross Smith[7] were signed by the Timbers in early February.

The Timbers began their preseason schedule on February 17 against the Portland Pilots men's team at Merlo Field in a match to benefit Mercy Corps and their relief efforts in Haiti.

[8] DeMartin, as well as former St. Pauli defender Ian Joy, rookie goalkeeper Matt Pyzdrowski and midfielder Derek Gaudet, were signed to contracts by the Timbers after featuring in the match.

[12] The returning players from the 2009 season saw their first action in a training match versus the Oregon State Beavers men's team in Corvallis on March 6.

Trialist O. J. Obatola scored the only goal as the Timbers defeated Seattle Sounders FC of MLS, who were also in their preseason, in front of 18,606 spectators at Qwest Field.

Kitsap defeated Portland 3–2 in a competitive match which saw Rodrigo López sent off by receiving two yellow cards in rapid succession after coming on as a substitute.

The Timbers made their final preseason player additions on April 7 when forwards O. J. Obatola and Bright Dike were signed to contracts.

The Portland Timbers began their 10th and final season in 2nd division soccer on April 17 by hosting the Rochester Rhinos at PGE Park.

[19] After earning a 1–1 draw with Montreal Impact in Portland's first road game of the year,[20] the Timbers rounded out a successful April with a 2–1 victory over Cascadia Cup rivals Vancouver Whitecaps FC.

[27] Hoping to build on their exhibition win versus Boca Juniors,[28] the Timbers returned to league play as they hosted Carolina RailHawks FC on June 6.

Ryan Pore again continued his scoring streak but Portland were thwarted by yet another stoppage time goal as Carolina earned a draw in the dying seconds of the match.

[30] Forward O. J. Obatola, who started six of the first seven league games and scored just one goal, had not played since the May 19 loss to Montreal and was released from his contract by mutual consent on June 10.

[33] Just two days later, the Timbers were back in league play as they welcomed expansion club NSC Minnesota Stars to Portland for the teams' first ever meeting.

Rookie forward Bright Dike recorded a hat-trick as the Timbers defeated the Pumas 4–1, ensuring Portland would meet long-time rival Seattle Sounders FC in the third round.

[36] Returning to league play on June 27, Portland continued its new-found momentum as the Timbers hosted expansion club FC Tampa Bay and came away 1–0 winners.

Sounders FC and former U.S. national team goalkeeper Kasey Keller made two saves during the shootout to help Seattle win 4–3 on penalties and knock the Timbers out of the cup for the second year running.

[39] Due to fatigue, head coach Gavin Wilkinson made eight changes to the side that faced Seattle and the reserves were able to earn a 0–0 draw to maintain their lead over Vancouver in the 2010 Cascadia Cup standings.

[41] A twelve-day break in league play allowed the Timbers to schedule back-to-back exhibition games versus foreign opponents.

Portland took advantage of being a man up when Timbers defender Mamadou Danso found the back of the net after a 72nd minute scramble in the penalty area.

They were unable to hold off the Timbers, though, as forward Takayuki Suzuki tallied his first league goal of 2010 in the 81st minute to give Portland a hard-fought 2–2 draw on the road.

A sold-out crowd watched as Minnesota took an early lead, but a third league goal from Bright Dike meant the score was tied 1–1 at halftime.

The celebrations were short-lived as one minute later Portland captain Ian Joy received a straight red card after a tackle on Stars midfielder Geison Moura.

[52] Hoping to avenge a July 28 3–0 loss in Missouri, the Timbers faced AC St. Louis for the fourth and final time of the season on August 14.

Ibad Muhamadu made his first start for Portland but it was Bright Dike that got the only goal of the game in the 41st minute to give the Timbers a much-needed 1–0 victory on the road.

[54] The Timbers enjoyed a rare week-long break between games as they prepared to face NSC Minnesota Stars for a fourth time with the series between the two teams even at 1–1–1.

With a man advantage, Portland's defense closed out the game and Pyzdrowski was credited with his first professional win and clean sheet as the Timbers won 1–0 in Minnesota.

[55] On August 25, Portland announced the signing of defender Kevin Goldthwaite, who had recently been released by New York Red Bulls, for his second stint with the Timbers after a loan spell in 2005.

[63] With the win against Puerto Rico — and help from other results around the league — Portland secured a playoff berth for the second year in a row.

Second Round winners advance to play one of 8 MLS clubs in 16-team knockout tournament Home teams listed on top of bracket The Cascadia Cup is a trophy that was created in 2004 by supporters of the Portland Timbers, Seattle Sounders and Vancouver Whitecaps FC.

The Timbers secured the 2010 Cascadia Cup—the club's second—on July 22 after defeating Vancouver 2–1 in a league match at Swangard Stadium in Burnaby, British Columbia.