The Portland Timbers are finally back in the MLS Cup Playoffs. No more Wild Card game stress, no more equivocating about "postseason" vs. "playoffs". It's the bona fide playoffs dangit, and the Timbers are in the big dance for the first time since 2021.
Awaiting them in Round One is the number one seed in the Western Conference. Portland will play in a best-of-three series against San Diego FC, who are enjoying perhaps the best season an MLS expansion side has ever had.
Here's everything you need to know about Portland's return to the playoffs in 2025, and how the Timbers stack up against San Diego.
"Wait... did you say best-of-three series?"
Sigh, yes I did. No, this isn't baseball, or basketball, or hockey. But this is a "whichever team wins two games advances" scenario like those other sports. And that's not an "aggregate goals with tiebreakers" series like previous MLS Cup Playoff iterations, or like, literally what the entire rest of the world uses.
The Timbers and San Diego will play tonight in San Diego, next weekend at Providence Park, and then if necessary the week after that back in San Diego. Those matches will all have a winner – no ties allowed (what is this, soccer?). Similar to the Leagues Cup, should a game be tied at the end of regulation there will be no extra time and the match will go straight to penalty kicks.
The first team to notch two wins advances, and the loser's season ends. It feels weird, but at least it's mostly straightforward.
"Sure... whatever you say. What are the Timbers' chances in Round One?"
Portland are 100% the underdogs in this series, make no mistake. San Diego is the number one seed for a reason, and they've earned that spot by playing some impressive soccer over the 2025 season. And of course, there is the Decision Day result where SD waltzed into a rain-soaked Providence Park and waxed the Timbers 4-0.
There is a strong argument that San Diego are a better team than the Portland Timbers. The expansion team should advance.
But that doesn't mean the Timbers don't have a chance. In fact, I think Portland actually has a semi-plausible path towards flipping the script and advancing.
"You're crazy, blog boy. How do they have that??"
Three reasons:
- There is precedent for an 8 seed toppling an expansion 1 seed in the West
- Portland's gritty Wild Card Game performance
- Playoff shenanigans
Two years ago, the Timbers found themselves in the same position that Sporting Kansas City was in. The Wiz qualified as an 8 seed through the Wild Card Game, and faced a number 1 seed then-expansion side St. Louis City SC in Round One. And what did SKC do? Steal game one on the road and then finish the job at home by winning game two. Sporting exploited STL's naivety and inexperience, and rope-a-doped them by being opportunistic and lethal.
To date, that's the first of only two times a lower seed has overcome homefield advantage and toppled a higher one in the Western Conference in Round One. But it was an MLS blue-blood taking down an expansion team they probably had no business beating... very similar to Portland's situation this year.
Plus, if Portland plays like they did against Real Salt Lake, they definitely stand a chance. The Timbers showed grit, familiarity, and experience in winning the Wild Card Round, and those are all factors that theoretically could make them a tough matchup in Round One. If Phil Neville has his side locked in again, doesn't get cute with formations or personnel, and if the players put in a shift like they did on Wednesday Portland can stand toe-to-toe with San Diego.
Sam Svilar
And that is all of course before you consider the ambiguous but undoubtedly real MLS Cup Playoff shenanigans that are sure to occur. Every year, it feels like something impossible happens. Last year, it was Atlanta United toppling the mighty fightin' Messi's of Inter Miami by one of the funniest moments I think that has ever happened in a soccer game (watch the Miami defender just spontaneously fall down in the middle of a defensive sequence):
I think about how Toto Aviles & Inter Miami went out in last year's playoffs all the time. I still can't get over that they all thought Atlanta would just stop playing here.
— Matthew Doyle (@mattdoyle.bsky.social) 2025-10-26T17:59:29.533Z
Penalty kick shootout ridiculousness (which Timbers fans know well!), teams turning into a pumpkin at midnight, players losing their minds on the field and doing something really silly (hey, we saw that on Wednesday!) – all of it tends to happen with a greater frequency in the postseason. The MLS Cup Playoffs are where the improbable can become real – like, say, the number 1 seed in the West suddenly losing their shooting boots.
Or, and this is very real, a breakdown in their team culture and locker room that has led to one of their star players potentially being iced out for the entire playoffs. Chucky Lozano, who did not appear on Decision Day, might actually not be a factor in Round One. If so, then that is a huge piece off the board that elevates Portland's chances ever so slightly.
"Okay, okay, fine. Let's entertain this for a moment: what do the Timbers have to do to pull this off?"
First and foremost, don't beat themselves. A big reason Portland lost on Decision Day was the myriad of missed passes and miscues that directly led to San Diego chances, and more than a few goals. SD is too well-drilled of a team for Portland to gift them any opportunities.
Tightening up the midfield is step one, and step two is progressing the ball quickly and efficiently through it. Portland's attack worked on Wednesday because there were clear ideas of where they wanted the ball to go and what they wanted to do with it once they got there. More of that will lead to goals in the series, more likely than not.
And it will likely come via counter-attacking opportunities – should Portland be able to make the most of them. San Diego will throw numbers forward and try to get the ball to the foot of Anders Dreyer or Amahl Pelligrino, and we saw what happens when that they are able to do so. The Timbers need to create more midfield solidarity, be coordinated with their press, and then be clinical and lethal with any numbers advantage they find on an attack.
Those are all tall orders, I know, but does it all sound completely impossible? I actually don't think so.
"Oh no... now you've got me feeling a dash of hope"
I'm sorry/you're welcome! The deck is stacked against the Timbers in these playoffs, and by all accounts their stay shouldn't last longer than November 8 at the latest.
But as I said, once you're in the big dance anything can happen. The Timbers might have just enough things break their way to pull it off. Regardless of what happens, we have at least 180 minutes of true playoff soccer to watch and stress about. Enjoy the ride, gang.
