Edmonton goaltender Ben Scrivens provided one, but it still was not enough. Mathieu Perreault tipped defenseman Jacob Trouba's point shot past Scrivens 17 seconds into overtime to give the Jets a 3-2 victory at MTS Centre.
"It was a struggle all game for us," Perreault said. "To find a way to battle through it and get a couple bounces our way, that made a difference. It was not the prettiest game we've played, but we got the two points, so at the end of the day, that's all that matters."
The loss extended the Oilers' winless streak to 11 games (0-7-4).
Scrivens stopped 23 shots and kept the Oilers in front 2-1 deep into the third period until Dustin Byfuglien's tying goal at 16:54.
"I thought we played a textbook road game," Oilers coach Dallas Eakins said. "We settled [into] the game. I thought we played a mature game, a mature road game. I thought we showed some growth from how we have played of late, and I believe that if we can bring that game every night, we're going to win a lot of hockey games."
Edmonton has not won since Nov. 9 against the New York Rangers. That victory at Madison Square Garden is one of the Oilers' two road wins in 12 games this season (2-6-4). With the loss Wednesday, the Oilers are 0-12-4 against Western Conference opponents, and their six wins are the fewest in the NHL.
Edmonton is 2-11-4 since a four-game winning streak that ended Oct. 29.
Along with two assists, Trouba also scored for the Jets for the first three-point game of his career, and Ondrej Pavelec made 22 saves.
The game began a three-game homestand for the Jets, who play nine of 13 games at MTS Centre in December. Winnipeg is 5-5-1 at home this season.
"There [are] no style points in the League," Jets coach Paul Maurice said. "If you go back and look at Edmonton's two prior games, they're battling hard on every puck and not making anything easy. That being said, we certainly didn't make it easy on ourselves with how we moved the puck. I thought [it] was a real challenge for us tonight."
Ryan Nugent-Hopkins and Teddy Purcell scored for the Oilers, who played without defenseman Nikita Nikitin for the second half of the game after he received a heavy hit from Winnipeg left wing Evander Kane.
"The way we had been playing really smart hockey, I definitely thought we would get two points," Oilers forward David Perron said. "It's one of those nights, we don't have too many of them, but it felt like we deserved two points, and we didn't do it."
Trouba gave the Jets a 1-0 lead when he finished a rush into the zone with a rising wrist shot past Scrivens at 12:33 of the first period. Winnipeg has scored first in seven straight games.
Trouba, a second-year defenseman who was the ninth pick in the 2013 NHL Draft, played a physical game and provided some relief for a defense that was missing Toby Enstrom (lower body) and Grant Clitsome (undisclosed).
"That's one of our strengths," Trouba said. "We're a big, fast team, and being physical is part of that. Especially against a team that has so many skilled players, it's important to try and slow them down as much as you can."
Nugent-Hopkins tied the game with 2:01 left in the first period when he beat Pavelec on a long shot through traffic for his sixth goal of the season. The goal also broke a 10-game goal-less streak for Nugent-Hopkins that dated back to Nov. 9.
The Oilers stripped Winnipeg defenseman Paul Postma of the puck inside the neutral zone. The turnover set up Perron to move into the Winnipeg zone and send a shot on net that Purcell deflected past Pavelec 1:31 into the third period for his fourth goal of the season and a 2-1 lead.
Edmonton was able to cling to the one-goal advantage through much of the third period and nearly went ahead by two on three occasions before Byfuglien tied the game with 3:06 left in regulation when he tipped Mark Stuart's shot past Scrivens for his fifth goal of the season.
"It was a lot closer to what we should be expecting of ourselves," Scrivens said of Edmonton's performance. "We've got to find a way to close that one out. Up 2-1 late, the team needs a save there. It's unfortunate I wasn't able to give them it tonight."
Scrivens, who is 0-6-3 in his past nine starts and has not won since Oct. 27, struggled to find positives after the latest loss.
"It doesn't matter what we deserve," Scrivens said. "We didn't get it. We've got to continue to work at things that we think are going to make us successful. Deserve and not-deserve, those all balance out at the end.
"There are some positives to build off of, but it's still frustrating to not be on the winning side."
The Oilers do not play again until Sunday when the San Jose Sharks come to Rexall Place.
"It's extremely frustrating not to get the win, but at the same time it's encouraging with how I thought we played a very mature game here on the road," Eakins said. "There's a laundry list of well-played, intelligent plays, mature plays, that we need to keep in our game. They had gone away from us, and now they're back, and we have to hold on to those. And that's how we'll go about it. We'll show our guys the things that they did very well, because they deserve it.
"It's frustrating knowing how this past month has gone, but I'm more encouraged than anything right now."