The Portland Timbers re-emerged in 2001 with the same spirit and passion for the game as the old Timbers of the North American Soccer League (NASL) days in the late 1970s and early 1980s. Since joining the United Soccer Leagues (USL) First Division, previously called the A-League, in 2001, the Timbers have quickly established a tradition of success in the Rose City - posting five winning seasons - and have advanced to the playoffs in four of the past six years.

The Timbers began play in 2001 at PGE Park and hired the services of Bobby Howe to be the club’s first head coach. Howe not only led the Timbers to a winning record (13-10-3) in their inaugural season; he also coached the Timbers to their first playoff appearance. The 2001 season was highlighted by the Timbers offensive trio consisting of all-league striker Mark Baena, Greg Howes and Major League Soccer veteran Darren Sawatzky scored 26 of the team’s 42 goals, and notched nearly half of the team’s assists on the season. The Timbers assembled a four-game winning streak early on, and won four of their last six matches to make the playoffs. Outscoring the Charlotte Eagles 5-2 in the two game series, the Timbers advanced to the second round of the playoffs. Their first season would end in the second round as the Hershey Wildcats shutout the Timbers in each of the two games in the series.

Opening the 2002 season with a five-game losing streak was not the way Coach Howe envisioned the start of the season, particularly after the successful campaign in 2001. But the Timbers fought their way back and finished the year with the club’s second consecutive winning season thanks to the offensive firepower of forwards McKinley Tennyson and Fadi Afash. Tennyson and Afash each scored 18 goals, and were among the league leaders in both goals and points in 2002. A 9-4 mark over the final month-and-a-half of the season propelled the Timbers into the postseason. In a tough home and home series, the Timbers faced the Vancouver Whitecaps in the first round and dropped both games by a 1-0 margin.

In 2003, the Timbers recorded the club’s third straight winning season with a 15-11-4 record, but for the first time in the team’s young history, they would not play in the postseason. The 2003 season saw an impressive four-game winning streak that included victories over playoff-bound clubs Vancouver and the Milwaukee Rampage. First-year Timbers forward Byron Alvarez led the team in scoring with 12 goals and 25 points, while midfielder Hugo Alcaraz-Cuellar set the single-season record for assists at nine. A mid-season addition, goalkeeper Josh Saunders, on loan from the L.A. Galaxy of MLS, helped the Timbers finish the year 10-4-2 over the last 16 matches.

The Timbers put together a record-setting season in 2004 as the club captured the A-League’s Regular Season Championship with an 18-7-3 record. Starting the season 6-0-0, the Timbers scored a club record 57 goals during the season – including two six-goal performances against the Edmonton Aviators. The defense also posted a record season, allowing just 30 goals in 28 matches, the fewest allowed by any Timbers team. Winning seven of their last 10 matches, the Timbers reached the postseason for the third time in four years. Battling the Seattle Sounders in the first round, the Timbers took a 2-1 aggregate goal advantage into the final game of the home and home series. But a 0-2 shutout by the Sounders ended the Timbers’ season as Seattle advanced with a 3-2 aggregate series win.

Taking home three league honors, rookie striker Alan Gordon was named the 2004 A-League Rookie of the Year after netting 17 goals, head coach Bobby Howe was voted the A-League’s 2004 Coach of the Year and general manager Jim Taylor was named the A-League's 2004 Executive of the Year.

In 2004, the Timbers also made a strong run in the Lamar Hunt U.S. Open Cup tournament. Entering the tournament in the third round, the Timbers defeated the Utah Blitzz of the USL’s D3 Pro League. In the fourth round the Timbers battled 2003 MLS Cup champion San Jose Earthquakes at PGE Park. In front of 10,622 fans, the Earthquakes, with U.S. national team member Landon Donovan, defeated the Timbers 3-0. The U.S. Open Cup is an annual tournament featuring both amateur and professional teams competing for the United States’ national soccer championship.

In 2005, the Timbers continued their winning ways and finished the year with their fifth straight winning season. Midfielder Hugo Alcaraz-Cuellar re-set the club’s record for assists in a single season, dishing out 12, and led the league in assists for the second straight season. With only one goalkeeper on the roster, Josh Saunders played every minute of the 2005 season. A seven-game winless streak in the heart of the season hurt the Timbers’ postseason positioning, but they finished with a 10-9-9 record. The Timbers suffered another disappointing first round exit in the playoffs at the hand of the Seattle Sounders. Seattle defeated the Timbers 3-0 in the aggregate score series on their way to the USL First Division championship.

Prior to the 2006 season, Chris Agnello assumed the head coach and general manager duties for the Timbers, replacing Bobby Howe who finished his career with a 76-64-26 record. The 2006 season would be the Timbers first losing season in modern franchise history, with a record of 7-15-6 and including an 11-game winless streak. Struggling to find consistency on the field, 29 players wore a Timbers uniform during the 2006 season. First-year Timber Luke Kreamalmeyer was the team’s leading scorer with eight goals, and was voted to the USL First Division All-League First Team. GM and coach Agnello left the organization following the season.

Former Timbers defender and assistant coach Gavin Wilkinson is now at the helm for the Timbers. Wilkinson, who also doubles as the club’s general manager, is the only player to have played in each of the Timbers’ first six seasons, 2001-2006. As a part of the winning tradition established early on, under Wilkinson the Timbers look to return to being a power in the USL First Division.