Ranking the top 10 moments in NHL Winter Classic history

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Is there any better way to ring in the new year than some outdoor hockey on New Year’s Day?

The NHL Winter Classic is back, with the St. Louis Blues and Minnesota Wild set to play at Target Field, home of MLB’s Minnesota Twins, in Minneapolis. After missing out on the notorious event last season due to COVID-19, hockey fans will be treated to the premier outdoor hockey event of the season. 

The Winter Classic has brought many great memories for the game of hockey, but which ones stand out the most?

Here are the top 10 moments in Winter Classic history. 

10. Corey Perry’s walk of shame

Less than three minutes into the 2021 Winter Classic between the Nashville Predators and Dallas Stars, Stars forward Corey Perry drilled Predators defenseman Ryan Ellis with an elbow to the head. He was assessed a five-minute major and a game misconduct, ending his night after just 38 seconds of time on ice. 

His walk to the locker room lasted almost as long. 

Perry’s extended route from the ice made for one of the most viral moments of the season and he certainly was on the butt end of a few Twitter jokes. 

Nashville scored two power play goals on Perry’s five-minute major, but the Stars rallied back to take down the Preds 4-2 at the Cotton Bowl in Dallas. 

9. Brent Seabrook hits Dan Cleary into bench

You want to make your presence felt early? How about drilling your opponent into your own bench less than two minutes into the game?

Chicago Blackhawks defenseman Brent Seabrook made sure Detroit Red Wings forward Dan Cleary’s 2009 Winter Classic was one to remember. Cleary went head over heels into the Blackhawks’ bench after Seabrook blew him up on his very first shift of the game. 

It sent the Chicago fans at Wrigley Field into an early elation. But Cleary and the Red Wings got the last laugh, winning 6-4 in the second Winter Classic. 

8. Mike Condon’s incredible glove save on Ryan Spooner

Things weren’t going well for the Boston Bruins in the 2016 Winter Classic against the Montreal Canadiens. Down 3-0 to their rivals at Gillette Stadium, the Bruins had an opportunity to get on the board with a power play late in the second. 

Bruins forward Ryan Spooner had a wide open net with three seconds left, but a slight hesitation by Spooner allowed Canadiens goalie Mike Condon to slide over to his left and make a fantastic glove save right before the buzzer. 

It just wasn’t meant to be for the Bruins, who fell 5-1 to Montreal. 

7. Pavel Datsyuk shows off silky mitts in shootout

Red Wings legend Pavel Datsyuk was known for his superb stick-handling ability. Just ask the 105,491 fans at The Big House in Michigan for the 2014 Winter Classic. 

With the Red Wings and the Toronto Maple Leafs knotted at 2-2, the two squads needed a shootout to settle the score. Datsyuk was tabbed as the second shooter for Detroit and he did not disappoint, faking the forehand shot, pulling it to his backhand and roofing it off the crossbar and in. 

The move seemed so subtle, but fooled Toronto goaltender Jonathan Bernier. Unfortunately for Datsyuk and the Red Wings, the Maple Leafs came out on top with Tyler Bozak potting the eventual winner in the shootout. 

6. Pavel Datsyuk splits the defense for go-ahead goal

More Datsyuk highlights? That’s what happens when you put “The Magic Man” in multiple Winter Classics. 

During the same game as the Seabrook hit, Chicago had built a 3-1 lead after the first period, but Detroit stormed back, having tied the game in the second period with two Jiri Hudler goals. 

With less than three minutes left in the middle frame, Datsyuk used his speed to split two Blackhawks defenders before beating goaltender Cristobal Huet five-hole with the dangle. 

It gave the Red Wings their first lead of the game, and Detroit hung on for the 6-4 win. 

5. Troy Brouwer’s last-minute, game-winning goal

At the 2015 Winter Classic, the Washington Capitals had built an early 2-0 lead over the Blackhawks at Nationals Park before Chicago came back to tie the game in the second. With less than a minute left in the third and the score still 2-2, it looked like for a second consecutive Winter Classic, regulation wasn’t going to be enough.

That was until Capitals forward Troy Brouwer spun around and fired a wrist shot past Blackhawks goaltender Corey Crawford with 12.9 seconds remaining. 

The former Blackhawk lifted the Capitals to their second Winter Classic victory with the 3-2 win, this time in front of the D.C. faithful.

4. J.T. Miller’s OT goal for the Rangers

The New York Rangers and the Buffalo Sabres met in the 2018 Winter Classic at Citi Field, marking the 10-year anniversary since the inaugural event.

After holding a 2-0 lead through the first 20 minutes, the Rangers allowed the Sabres to crawl back into the game and overtime was needed to settle the score. 

Sabres forward Jacob Josefson took a tripping penalty in the extra frame that proved fatal to the Buffalo comeback, as Rangers forward J.T. Miller cleaned up a rebound on the power play for the OT win. 

The win for New York made it two-for-two for the franchise in Winter Classics and the second time a Winter Classic was decided in overtime. 

3. Marco Sturm's OT goal for the Bruins

Fenway Park has been home to many memorable moments in baseball history, but there’s one hockey highlight you have to add to the list. 

In the 2010 Winter Classic between the Bruins and the Philadelphia Flyers, Bruins forward Mark Recchi tied the game 1-1 with his power-play goal with less than three minutes left in the third. For the second time in the three Winter Classics up to that point, overtime was needed. 

Bruins forward Marco Sturm sent the Fenway crowd in a frenzy, tipping home a pass from Patrice Bergeron for the win. 

It was the first time a home team had won a Winter Classic game and the first OT winner in Winter Classic history.

2. Henrik Lundqvist stones Danny Briere on the penalty shot

The Flyers had the perfect opportunity to tie the game late at the 2012 Winter Classic. 

Down one with 20 seconds left, the Flyers were awarded a penalty shot after Rangers defenseman Ryan McDonagh was whistled for closing his hand on the puck in the crease. The Flyers sent Danny Briere out to get the game-tying goal. 

King Henrik had other ideas. 

Henrik Lundqvist stopped Briere’s shootout attempt to secure the 3-2 win for the Rangers. Yet another clutch moment for one of the greatest goaltenders of all time. 

1. Sidney Crosby wins first Winter Classic in a shootout

Hollywood could not have scripted a better ending to the first-ever Winter Classic in 2008. 

In the snowy conditions of Buffalo, the Pittsburgh Penguins and Sabres needed a shootout to decide the inaugural event, with the score knotted at 1-1. The Penguins needed just one more goal in the shootout to win with then-20-year-old captain Sidney Crosby up next. 

And the No. 1 pick in the 2005 draft delivered. 

Crosby snuck one through Ryan Miller’s legs as the Penguins won the inaugural Winter Classic with the 2-1 victory at Ralph Wilson Stadium (now known as Highmark Stadium), home of the NFL’s Buffalo Bills. 

The snow, the circumstances, the player -- it’s a moment in Winter Classic history that likely will never be topped. 

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