The latest deflating performance came on Sunday night at Children's Mercy Park, where the Timbers came from behind to nab a 2-2 draw against a Sporting Kansas City team enduring their worst season in nearly a decade and already eliminated from postseason contention.
The Timbers are now winless in five straight games dating back to the beginning of the month when they came from behind to beat this very same Kansas City team — a team that is also winless in five, having blown leads in each and every one of those games.
For two of the Western Conference's most respected, most competitive clubs, Saturday night's game, played in front of a sparse crowd, was a rather pitiful affair.
It was plenty entertaining — the three red cards, four goals, and late penalty saw to that — but neither team played with anywhere near the discipline, tempo, or skill required to compete seriously at this stage of an MLS season.
Sporting strung together their share of fine buildups, but were characteristically sloppy in front of goal and soft at the back when they could least afford it. The Timbers, meanwhile, were limp and directionless going forward and again fell asleep defensively at the start of a half.
They got the individual moments they needed to salvage a point, thanks again to Sebastian Blanco and Jeremy Ebobisse, but this was no more a convincing performance than the Wednesday night's draw against New England was.
The Timbers' only saving grace at this juncture is that the two teams they are jockeying with for the Western Conference's final two postseason places are also in horrifying spasms of form: San Jose has lost five straight games; FC Dallas is winless in four.
The scenario for Portland going into their final match of the season next Sunday against the Earthquakes is straightforward. Win or draw, and they're in. Even if they lose, and Dallas fails to beat what will be a shorthanded Kansas City side in Frisco, they'll qualify anyway.
What will they be able to do in the likely event that secure a postseason berth? If the last six weeks are any indication, very little.
The team looks tired, and for good reason. Its best player is locked in a contract dispute that has cast a pall over the entire club. Its star forward has scored in just three of his last 14 appearances and is now set to be suspended for the team's final regular season game.
Most importantly, though, the Timbers have failed take any major steps forward since they began to struggle in August. Giovani Savarese has largely done a terrific job in his time at the helm, but he doesn't appear to have any answers right now.
He's just doing his best to keep fresh bodies in the lineup. To that end, even before the red cards came out on Saturday night, the Timbers were shorthanded: Ebbobise, Diego Valeri, Jorge Moreira, and Cristhian Paredes were all on the bench, while Larrys Mabiala was absent entirely serving a suspension of his own.
Unsurprisingly, given the absences, the Timbers started the match on the back foot — getting outshot 9-0 in the first half of the period, with 17-year-old Sporting midfielder Gianluca Busio coming closest to opening the scoring when he rocketed a shot off of the crossbar of Steve Clark's goal after just five minutes.
With nothing in particular to play for, Sporting was drawing their fullback and midfielders high up the field, attacking with numbers, and, in the process, placing a great deal of responsibility on the shoulders of their central defenders.
But Sporting failed to take advantage of their reprieve. Just three minutes later, Felipe Gutierrez, under no pressure whatsoever, overhit a long ball to the wing for Graham Zusi — which Zusi, in effort to prevent the ball from sailing out of play, headed straight back into the middle of the field.
It was the wrong decision. Blanco pounced on the ball and turned upfield to lead the Timbers in a four-against-three counter, slipping a ball wide for Marvin Loría, whose deflected cross fell perfectly back to Blanco to slam in off of the underside of the crossbar.
It wasn't quite the jaw-dropping goal he scored in Kansas City in the second leg of the Western Conference championship last year, but it was some kind of effort, and it produced a familiar celebration as the Argentine ran to the corner in front of the Cauldron pounding his chest.
One minute later, though, the good vibes were summarily dispelled. Johnny Russell took a pass on the wing from Roger Espinoza, fired a cross into the middle of the box, and raised one arm in celebration as Krisztian Nemeth slipped behind Claude Dielna and nodded it in to level the score.
There was some question about whether Russell was onside when he received the ball, but there was no stoppage for a video review check. The goal stood, and the fireworks, somehow, were just getting started.
Five minutes after the equalizer, Nemeth's first goal since mid-May, Gutierrez dragged down Fernandez on a break and started screaming at him about a play that had unfolded several minutes earlier.
Fernandez responded with a similar amount of vigor, and moments later both teams had come together in a full scale confrontation. When the dust settled, Fernandez had been issued a red card for putting his hand to Gutierrez's neck, as had Espinoza for grabbing Blanco's throat.
Whether Fernandez's conduct warranted a red card was on the touchline and will continue to be a topic of intense debate. What there can be no doubt about is that, when the teams retook the field for the commencement of the second half, the Timbers fell asleep.
Straight off the kickoff, as Sporting came up the field, Russell wove his way through a crowd of Portland defenders into the penalty area. The ball deflected Busio, who struck it off of the post, and Daniel Salloi was able to muscle the rebound past Zarek Valentin to score his first goal of the year and make it 2-1.
The game, with that, entered an odd state: entirely open, with acres of space for either side to exploit, but simultaneously played at a near-ponderous pace — the Timbers disjointed, Sporting refusing to kill them off.
With his team chasing a goal, Savarese quickly brought on Ebobisse and Dairon Asprilla. Valeri, though, was left on the bench. It was an exceedingly odd decision. But given the way Kansas City's season has unfolded, their failure to score a third goal was always likely to cost them.
Sure enough, with less than ten minutes to play, the Timbers rescued themselves. Blanco received the ball on top of the box, turned, and cut out two defenders with an excellent pass for Ebobisse — who was dragged down as he received the ball through on goal.
Referee Alan Chapman wasted no time in pointing to the spot, and then reducing Sporting to nine players as Ilie got his marching orders for the foul.
Sporting goalkeeper Tim Melia had saved all three penalties he'd seen in 2019, but with Valeri looking on, Asprilla stepped up and blasted his shot in to maintain his own perfect record from the spot, score his first regular season goal in nearly 14 months, and provide a fitting end to a truly bizarre evening.
The Timbers will move on to fight another day. But now even they must know that the time they have to figuring themselves out before they start playing elimination games has all but run out.