But in between, they laid the foundation for an improbable playoff push, grinding out a 1-0 victory against the Supporters' Shield-contending Colorado Rapids on Sunday afternoon at Providence Park. A win against the already-eliminated Vancouver Whitecaps on Decision Day next Sunday (4pm ET; MLS LIVE) could put Portland into the Audi 2016 MLS Cup Playoffs.
Hanging over their heads, however, is a winless road record.
The Timbers have been among the best home sides in Major League Soccer, winning more home games than every Western Conference side except league leaders FC Dallas, but they have not won a single game away from the raucous confines of Providence Park. For the team to secure a spot in the playoffs, that will almost certainly need to change.
"For us to have 12 [home] wins, which is a club record, and to still not be in is tough," said Timbers head coach Caleb Porter. "If you look at our season, it is a tale of two seasons. Our season at home has been as good as ever since I have been here, in the way that we have played and the way that we have gotten results. On the road, it has been the complete opposite."
Still, the Timbers can take heart from their history of getting big wins north of the border, including a victory in the 2015 Western Conference Semifinals on their way to raising last season's MLS Cup.
"We have had some really good games in Vancouver," Porter said. "We play really well there. We have won there twice since I have been here and [Jack Jewsbury] smashed a game-winner there to win the Cascadia Cup [in 2012], so we are excited."
Jewsbury, who is retiring after the 2016 season and was honored in a pregame ceremony from the Timbers, took a more pragmatic look at the Timbers' final match of the regular season.
"It is do or die when we go to Vancouver," Jewsbury said. "That gets you ready for the playoffs, where you have got to win or you are going home and the season is over. That was the message from Caleb coming into today: If we don't get a win, our season could be over if some other results don't go our way. And guys stepped up. I think that with this group, what you have seen is that when our backs are against it a little bit, everybody steps up and you get our best."