It's what we've all been waiting for: For the first time since 2021, the Portland Timbers are back in the first round of the playoffs. Do Western Conference-topping MLS newcomers San Diego FC present a seemingly-insurmountable task for the Timbers? Absolutely. Did the Timbers wash away all of the skepticism surrounding their last few months of the season, or Decision Day drubbing at the hands of their first round opponents? Absolutely not.
Regardless, these are the moments you live for as a supporter. An opportunity for your club to, no matter how daunting the task at hand is, start the business end of the season with a 0-0 record with the dream of reaching the summit once again.

Like I said, tonight represents the first clash of a best-of-three series against San Diego FC (Kickoff scheduled for 6:30 p.m. PT on Apple TV) feeling mighty good about themselves. They became the second-ever MLS expansion side to win their conference in their debut season (St. Louis City SC, 2023), and secured that feat by drubbing Phil Neville's Timbers 4-0 on Decision Day just one week ago today.
However, there are a couple of things that should inspire confidence in Timbers supporters heading into the series:
The Timbers secured a 0-0 draw in San Diego earlier this season
Although the form of the regular season goes out the window when the postseason begins (See Atlanta United knocking #1 seed Inter Miami CF out of the playoffs in the first round last season), the Timbers do have a proof-of-concept result against a very tough San Diego team.
Back on August 23 the Timbers went to Snapdragon Stadium and left with a huge point with the help of a couple San Diego goals called back for offside. The Timbers were out-shot and out-possessed on the day, but actually did have a higher xG (1.6 to 1.0) and put more shots on-target (2 to 1) than their hosts.
In a best-of-three series where a draw in regulation gives you a shot to earn a win via penalty shootout, that match earlier this season should very much be the blueprint for the Timbers tonight.
All of the external pressure is on San Diego
The playoffs are all about momentum, and there aren't many better ways to gain some than overcoming a win-or-go-home Wild Card game in front of your home crowd. Especially when the victory is the first under a new head coach after four years of disappointment.
The win against Real Salt Lake was vital for the Timbers as a club and fanbase to restore a glimmer of hope in what they're doing. All of the external pressure in this series is on San Diego as the conference champions, and none of it is on Portland as heavy underdogs.
That means players like Kristoffer Velde, Pipe Mora (fresh off a brace), David da Costa, and Antony – all of whom have looked to be carrying around a literal ton of pressure on their shoulders – the opportunity to play freely.