Golden Boot winner Valentin ‘Taty’ Castellanos scored in the opening half and it appeared that New York were on their way to the championship before Portland’s Felipe Mora scored in stoppage time to make it 1-1.
Neither team managed to find the net in extra time, before Alexander Callen’s penalty sealed the 4-2 shootout victory.
New York City FC won the MLS Cup title for the first time – just six years after they joined the league
Alexander Callen (right) scored the winning penalty in a 4-2 shootout win over the Portland Timbers
Manager Ronny Delia celebrated after the game by stripping to his underwear and doing push-ups
Goalkeeper Sean Johnson saved attempts from Mora and Diogo Valeri to swing the match into NYCFC’s favour.
The winners celebrated in front of the goal after Callens converted, while Valeri lay in the centre of the pitch in disbelief.
A group of New York players broke off from the party to salute their fans, grouped in the opposite corner of the stadium.
Former Celtics boss Ronny Delia was left in tears before celebrated by stripping down to his underwear on the pitch and doing push-ups in front of the trophy before hoisting it up in the air.
Delia had promised before the game he would strip to his underwear if they were to take the victory.
The club which joined in the league 2015, had never advanced to the title-deciding game until now.
Castellanos, who scored 19 goals in the regular season, was back in the starting lineup after missing the Eastern Conference final against Philadelphia.
The Argentine striker was handed a red card in the conference semifinals against the top-seeded New England Revolution, which NYCFC won on a penalty shootout after a 2-2 draw.
Valentin Castellanos (left) scored the opening goal to give New York City FC the lead
New York’s 2-1 victory over at Philadelphia secured them a place in the MLS Cup final for the first time.
They were the fourth seed in the East after finishing the regular season with 14 wins, 11 defeats and nine draws.
The Timbers were also seeded fourth after holding a 17 win, four defeats and 13 draw record in the regular season.
Portland downed the top-seeded Colorado Rapids on Thanksgiving Day before beating Real Salt Lake 2-0 at Providence Park to win the Western Conference and secure home field for the final.
The Timbers won an MLS Cup in 2015 and went to the final in 2018 but fell to Atlanta.
Portland Timbers forward Felipe Mora celebrated in stoppage time to take the game to extra-time
Portland saw the return of Dairon Asprilla, who was suspended for the match against RSL because of a late red card in the victory over the Rapids.
Timbers playmaker Sebastian Blanco, who sustained a hamstring injury against the Rapids and didn’t play against RSL, also returned to the starting lineup. Blanco has seven goals and seven assists this.
The game was chippy at the start, with a brief skirmish breaking out in the 25th minute. Players also had do endure rather nasty weather conditions, with temperatures in the 40s, steady rain and gusty winds.
Castellanos scored on a header off a free kick from Maxi Moralez in the 40th minute, giving NYCFC the early lead. The goal celebration was marred when it appeared that one of that New York’s Jesus Medina was struck by an object thrown by a fan.
Goalkeeper Sean Johnson was the MVP after making two saves during the penalty shoot-out
It was the first set-piece goal that the Timbers had allowed in 20 games.
The Timbers at times looked disorganized. Mora had one of the best chances for Portland in the second half, but his shot in the 81st minute fell directly in the hands Johnson.
Mora had another chance on a header off a cross in the 97th minute but it sailed well over the net.
He finally broke through in the final minute of four-minutes of stoppage time. It was the latest goal ever scored in regulation in an MS Cup.
But the goal was controversial as New York players argued that it should be disallowed, claiming that Maxime Chanot was fouled by Portland’s Larry Mabiala in the run-up to the finish.
New York City FC joins parent club Manchester City by winning the title
New York City FC were the fourth seed in the East heading into the play-offs from the regular season
Valeri came in as a sub in the 89th minute amid speculation about whether the 35-year-old will retire.
Valeri was with the Timbers when they won the MLS Cup in 2015, scoring in the opening moments of the 2-1 victory over the Columbus Crew. He was named the league’s MVP in 2017 after racking up 21 goals and 11 assist.
NYCFC joins parent club Manchester City in the Abu Dhabi-funded group in winning a title.
The group now partially or completely owns NYCFC and Manchester City, as well as teams in Australia, Belgium, China, France, India, Japan, Spain and Uruguay with a partnership in Bolivia as well.
Owner Sheikh Mansour’s takeover of Manchester City in 2008 that transformed the fortunes of a team with little track record of success into the Premier League’s most successful team over the last decade.