Daniel Alfredsson scored the winner in the tiebreaker, and Detroit escaped Toronto with a 5-4 victory over the Maple Leafs on Saturday night in a Winter Classic preview.
The Red Wings had lost 11 straight shootouts, six this season.
"It was a mental block for us," Alfredsson said. "To win this one, hopefully we can put that behind us and start winning a few. Winning in overtime last game and now winning in a shootout tonight lessens the grip on the stick next time around."
Detroit coach Mike Babcock wasn't too hung up on his team's struggles in shootouts. But he was quite pleased to have a two-game winning streak after his club dropped six straight.
"I think we're a pretty even-keeled group," Babcock said. "We just keep on keeping on. We're going to be fine here in the end. We've got to get players back, and then we'll start playing with some speed and confidence and tempo and everything."
The Red Wings were playing without injured captain Henrik Zetterberg (back), goalie Jimmy Howard (knee), center Stephen Weiss (sports hernia), and forwards Gustav Nyquist (groin), Johan Franzen (concussion) and Justin Abdelkader (concussion). They got defenseman Danny DeKeyser back after he missed 15 games with a shoulder injury.
Tomas Tatar scored for Detroit with 6:16 left in regulation to tie it at 4.
"We score the first goal and then we basically stood around for the rest of the period and watched them do their thing," Toronto coach Randy Carlyle said. "They outcompeted us badly in the first period."
The teams will meet again in the Winter Classic at Michigan Stadium in Ann Arbor on Jan. 1.
"We'll take the point," Maple Leafs captain Dion Phaneuf said. "Coming back, I feel that was a big step for our team to come back against a team that doesn't really give up a whole lot. We did a lot of really good things."
"Definitely not what we had in mind, what I had in mind," said Reimer, who made a third straight start for the first time this season. "They just scored a couple too many goals.
"Obviously, the second one, that can't go in. It was obviously my fault, a hundred percent. And the third one, they made a nice play, but I think that's one that I can get done on some days, too."
Former Maple Leafs goalie Jonas Gustavsson gave up four goals on 23 shots, then stopped James van Riemsdyk, Lupul and Mason Raymond in the shootout. It was Gustavsson's third straight start as his workload has increased with Howard injured.
"I don't think I had my best game," Gustavsson said. "At least we were able to step up there and get the win."
Datsyuk also scored in the shootout for Detroit.