Portland Timbers stalwart Diego Chara has confirmed he will retire after the 2027 MLS Sprint Season.

With MLS' schedule set to change next year, there will be a shortened, 14-round regular season between February and April in 2027.

The playoffs will then take place in May, before the 2027-28 campaign starts later in the year.

However, Chara will bow out after Portland's Sprint Season is over.

Chara joined Portland ahead of their inaugural MLS campaign in 2011. He has played the most MLS games for the Timbers (450).

He has scored 13 goals and provided 38 assists for the Timbers in all competitions.

"The performances I had during the season give me that confidence as well [as] the support of my team-mates, coaching staff, by the club. That gives me the strength to continue," Chara said as he prepares for the run-in of what will now be his penultimate MLS campaign.

"It's going to be really good and I'm really happy to have the opportunity to be back for next year.

"Being for this long with the team, being one of the 'original Timbers,' I think is the best way to finish this career with the Timbers."

Chara's first game post-announcement comes on Wednesday, as the Timbers face St. Louis City SC.

After tying the longest regular-season unbeaten run in MLS history at 19 games, St. Louis City have lost two straight matches.

With three regular-season games remaining, the Timbers are still in playoff contention, while St. Louis City sit pretty in third place in the Western Conference.

A look back at 16 seasons https://t.co/H4olQWiwWB

— Portland Timbers (@TimbersFC) October 27, 2026

PLAYERS TO WATCH

St. Louis City – Rafael Navarro

Navarro has netted 18 MLS goals this season, and though St. Louis City's place in the playoffs is ensured, he will be eager to end the regular campaign on a high note.

Portland Timbers – Eric Izoita 

Izoita assisted two of the Timbers' three goals in their win over Charlotte FC on Saturday.

At 19 years, 46 days old, Izoita became the youngest player in Timbers history to record multiple assists in a match, surpassing Cristhian Paredes' two assists at 19 years, 331 days in April 2018.

MATCH PREDICTION: ST. LOUIS CITY WIN

The seven regular-season meetings between St. Louis City and the Timbers have been split evenly, with each team winning twice (D3) and scoring 12 goals.

Both teams have recorded a home win and a road win over the other in league play.

The Timbers have won just two of their last 23 away matches in all competitions dating back to August 2025, with both wins coming on the west coast (at San Diego FC and the Seattle Sounders).

Portland have not won outside of the Pacific time zone since a 4–2 win at Sporting Kansas City on April 13, 2025.

OPTA WIN PROBABILITY

St. Louis City – 53.1%

Draw – 21.6%

Portland Timbers – 25.3%