In 2013, the Timbers finished the regular season in first place in the Western Conference, clinching both their first-ever playoff appearance and a CONCACAF Champions League berth.

In 2021, the Timbers won the Western Conference and once again were runners-up in MLS Cup, falling to New York City FC 4–2 on penalties after a 1–1 score at extra time.

[4] The biggest issue for the city of Portland at that time was that due to league concerns about seating configuration, field surface and scheduling, obtaining an MLS club would require a new stadium.

[4] MLS was in support of the proposal, wanting to continue to expand the number of owners in the league (for a while, all of its teams were owned by three men: Philip Anschutz, Lamar Hunt, and Robert Kraft).

[4] Though supporting the acquisition of an MLS franchise raised numerous issues for Mayor Sam Adams and the Portland City Council,[7] the Timbers were announced as Major League Soccer's eighteenth team on March 20, 2009, by Commissioner Don Garber.

[12] Immediately after the Expansion Draft, the Timbers announced the trade of their first pick (midfielder Dax McCarty), from FC Dallas to D.C. United for defender Rodney Wallace.

An important player was Diego Valeri, whom the Timbers had acquired from Club Atlético Lanús on loan with an option to purchase (which they exercised later in the season).

In a highly competitive Western Conference, the Timbers once again qualified for the MLS Playoffs, finishing strong in the final matches of the regular season which included a 5–2 win against LA Galaxy.

[29] Portland's 2016 offseason consisted of transfers of key players including Jorge Villafaña, Will Johnson, Maxi Urruti, and Rodney Wallace.

[37] Despite starting their 2018 season without a win in their first five games, Savaraese and the Timbers finished their campaign strong, and would earn their second trip to the MLS Cup on December 8, 2018, where they would be defeated 2–0 by Atlanta United.

[40] The Timbers began the 2020 Major League Soccer season with a loss at home against Minnesota United FC and a win against MLS expansion side Nashville SC.

[43] The Timbers defeated Chicharito and the Galaxy 2–1 to open the tournament, downed Houston by the same score 5 days later, and then, assured of passage to the next round, came back to tie LAFC 2–2 while playing mostly their reserves to finish on top of the group.

In the Round of 16, Portland led FC Cincinnati before a late gaffe from goalkeeper Steve Clark forced the Timbers into a tie and penalty kicks.

In the Round of 8, Portland fell behind New York City FC after conceding an early goal but scored 3 in a row in the second half to cruise to an easy 3–1 win, which was capped off by a stunning outside-the-box strike from Andy Polo.

[44] Playing the Philadelphia Union next in the semifinals, the Timbers rose to the challenge with goals from Jeremy Ebobisse and Sebastián Blanco and held on to score a 2–1 victory and advance to the finals for the club's first title game appearance since the 2018 MLS Cup.

In the MLS is Back Tournament championship game against hometown Orlando City, Portland opened the scoring with a diving header from Larrys Mabiala off a pass from Diego Valeri in the 27th minute.

[46] In 2021, the Timbers finished fourth in the Western Conference, then upset top-seeded Colorado Rapids and staved off a hot underdog in Real Salt Lake en route to their third Cup final as an MLS club.

After a 94th-minute goal from forward Felipe Mora that canceled out a first-half score from league top-scorer Valentín Castellanos, the Timbers and NYCFC finished extra time levelled at 1–1.

[47] The investigation led to widespread fan discontent, focused primarily on the fact that Riley was both hired and fired by Timbers/Thorns owner Paulson and GM Wilkinson.

[50] The Yates Report, released on October 3, 2022, found further transgressions by members of the Timbers and Thorns organization, including alleged inappropriate conduct by president Mike Golub.

[51] The report and pressure from fans prompted Alaska Airlines, Tillamook, KeyBank, and other corporate sponsors to withhold, redirect, or cancel their financial contributions to the club.

On the pitch, the Timbers would lose the last game of the season against Real Salt Lake, knocking them out of playoff contention and lifting RSL in their place by one point.

After narrowly missing the playoffs yet again, the club would go on to hire Phil Neville as coach, which brought ire from fans due to past sexist comments on social media.

[67] Alaska withdrew their sponsorship at the conclusion of the 2023 season, a year after it donated a portion of its financial contributions to the NWSLPA in response to allegations of abuse within the Thorns organization.

[69] The sponsorship was terminated one game into the regular season by the Timbers on February 28, 2024, after DaBella CEO Donnie McMillan Jr. was accused of sexual harassment.

The new remade steel stand was inspired by the legendary Boca Juniors' stadium La Bombonera as well as the classic raised stage of Shakespeare's Globe Theatre, creating a unique layered appearance that also paid homage to the original, unfinished 1926 Multnomah Field plans.

[91] A protracted public battle between the Army and MLS brass occurred, culminating in a protest during the August game against Seattle where the TA deliberately stayed silent for the first 33 minutes of the nationally televised clash to commemorate 1933, the year that the Iron Front was disbanded in Nazi Germany.

Members of the supporting groups between the two clubs even jointly celebrated together after Vancouver eliminated Portland from the 2010 USL Playoffs due to the shared move to MLS the next year.

[105] In January 2020, Timbers midfielder Sebastian Blanco said that LAFC was Portland's biggest rival outside of Cascadia, and that he "loves to play those games" against them and the LA Galaxy.

Joey continues Jim's trademark of cutting a round (or "cookie") from a large log with a chainsaw every time the Timbers score a goal.