Philadelphia had three points and a victory until, literally, the final 30 seconds of the match.
A teamwide brain cramp by the Union, however, led to a Portland corner kick that resulted in Timbers striker Gaston Fernandez scoring on a header on the last play of the game.
"To get the lead and give one up in injury time is a tough way to lose out on a couple of points," Union manager John Hackworth said, "but Portland is a really good team and for us there is just a lot to build off."
Hackworth was right because this new-look Union roster, featuring a host of newcomers in the starting lineup (forward Cristian Maidana, midfielders Maurice Edu and Vincent Nogueira and defender Austin Berry), did a lot of good things.
With free-agent signees Edu and Nogueira teaming with holdover Brian Carroll, the midfield played with creativity, possession and control - things it sorely lacked in 2013.
With Berry joining holdovers Amobi Okugo, Fabinho and Raymon Gaddis, the defense was solid.
The new 4-3-3 had Maidana up front with Jack McInerney and Sebastien Le Toux looked aggressive and dangerous instead of passive and stagnant.
McInerney, whose 2013 campaign was as baffling as it was promising, scored in the 64th minute to give the Union a 1-0 lead.
For 92 minutes and 30 seconds, the Union played like the revamped and improved team that it has promised to be in 2014.
"We've come in with a different formation and a bunch of new players and I think we held our own," said McInerney, who had a team-high 12 goals last season but had a scoring drought of more than 4 months. "We played well and, as the season goes along, I think we are only got to get better.
"If you would have told us that we would have drawn 1-1, I think we would have taken it. But giving up late goals is something that is going to have to change if we want to make it into the playoffs."
That's exactly right because returning to the playoffs for the first time since its lone postseason experience in 2011 is the lowest of the expectations for this franchise that is starting its fifth season.
So it was disheartening to see an old bugaboo again rear its ugly head in what is supposed to be the start of a new era for the Union.
"We did a lot of that last year where we gave up late goals that cost us points," McInerney said.
What happened in the final 30 seconds against Portland was simply a remarkably silly display of a lack of game awareness by the Union.
It started with the Union failing to hold the ball in the Portland zone when it was trying to run out the waning moments of extra time.
Then when the ball went out of bounds for a Portland corner kick, several Union players had not gotten back into the defensive zone.
With Union players scrambling to get into position into the penalty box, Timbers midfielder Will Johnson hurriedly took the free kick.
The Union players were not set, organized or in solid defensive positions when Johnson sent a low drive that deflected off the leg of Carroll.
The ball went to Fernandez, who was camped, unmarked, a few feet from the goal line between Gaddis and Antoine Hoppenot with a yard of space on each side of him.
Fernandez easily headed the ball into the net for the equalizer.
Certainly, there was some bad luck involved with the deflection off Carroll going to Fernandez, but good teams make their own good luck and bad teams create their own bad luck.
Portland won the West in 2013. The Union missed the Eastern Conference playoffs by three points.
Philadelphia learned how precious points are a year ago.
Last season, the Union was one point out of first place in the Eastern Conference with eight matches to play.
But Philadelphia closed by finishing 2-4-2, notching just eight of a possible 24 points.
Obviously, that line of thought has to be tempered by the fact that Saturday's opener was on the road against a top team.
Still, it will be interesting to see how this remade Union responds on Saturday in its home opener at PPL Park against the New England Revolution.
"It feels more like a loss than it does a win," Hackworth said of the draw with Portland. "I guess that's a good thing because the players know we gave away two points. We did enough to get three and we have to clean up some game-management issues and learn how to close it out a little bit."