The 2023 NHL Winter Classic is quickly approaching. Sidney Crosby’s Pittsburgh Penguins travel to Fenway Park to face the Boston Bruins in hockey’s biggest annual outdoor game.

The Winter Classic is relatively new, all things told. Hockey fans watch the first iteration on New Year’s Day 2008 live as snow fell upon a passionate Buffalo, New York crowd.

Since then, we have seen incredible matchups and amazing moments as the NHL takes us back to the sport’s early days. And we are certainly in for many more incredible moments as the Winter Classic continues to roll on.

With no further ado, here are the five best moments in NHL Winter Classic history, ranked.

5) Magic in the nation’s capital

The 2015 NHL Winter Classic emanated from Washington DC. The Washington Capitals hosted the Chicago Blackhawks on New Year’s Day in front of nearly 43,000 people.

Chicago fell down 2-0 early on after Capitals forwards Alex Ovechkin and Eric Fehr found the back of the net. However, they battled back, tying the game at two in the second period thanks to Brandon Saad’s ninth of the season.

The third period was quiet up until the very end. Washington won a faceoff at center ice, and found their way into the offensive zone. Ovechkin’s stick broke, causing him to lose the puck.

Thankfully, former Blackhawk Troy Brouwer ripped a shot past Corey Crawford’s glove. And with 12.9 seconds left, Brouwer put his former team to the sword. Washington won 3-2 in front of their home fans.

4) King Henrik stands tall

The Philadelphia Flyers couldn’t have written a better script if they tried. In the 2012 Winter Classic, Philadelphia was down 3-2 late in the third period, and they were given a gift.

Rangers defenseman Ryan McDonagh slid into the crease in an attempt to block the puck from crossing the goal line. He was called for covering the puck in the crease, and Philadelphia were awarded a penalty shot with 20 seconds left.

Flyers forward Daniel Briere skated in, attempting to goad Rangers goalie Henrik Lundqvist into making a move. However, King Henrik stood tall, and made the crucial save. New York held on to win the game, which gave them the league’s best record at the time.

3) Marco Sturm, overtime hero

As it stands, Marco Sturm is one of the most underrated players of his generation. He certainly is one of the greatest German players to ever play. And in 2010, he proved why.

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Sturm’s Bruins found themselves tied with the Flyers 1-1 with a little over three minutes left in overtime. Boston moved the puck up the ice, looking to end the game before the dreaded shootout.

Bruins forward Patrice Bergeron won a battle along the boards and floated a pass toward the goal. Sturm, ever the opportunist, moved in position in front of Flyers goalie Michael Leighton.

Sturm poked the puck passed the Philadelphia netminder. His 14th goal of the season gave the Bruins a massive 2-1 win in one of the greatest Winter Classic’s ever played.

2) Datsyukian Brilliance

The sheer beauty of this goal alone puts it this high on this list. In the second Winter Classic ever, Red Wings forward Pavel Datsyuk did what he did best: score another iconic goal.

The hosting Blackhawks actually set the tone early. Chicago defenseman Brent Seabrook sent Detroit forward Daniel Cleary into the Blackhawks’ bench with an insane hit in the first period.

The Blackhawks raced out to a 3-1 lead in front of a rowdy Wrigley Field crowd. However, the Red Wings came back. Detroit forward Jiri Hudler scored twice to level the game at three.

That’s when Datsyuk took over. The Russian superstar took the puck through the Blackhawks defense and left Chicago goaltender Cristobal Huet out to dry. His goal made it 4-3 Detroit, and they went on to win 6-4.

Detroit goaltender Ty Conklin also made notable history in this game. He became the first player to skate in every outdoor game up to that point. He played in the 2003 Heritage Classic and the 2008 Winter Classic.

1) Sid has ice in his veins

Speaking of the 2008 Winter Classic, our number one entry comes from the very first Winter Classic. Sidney Crosby delivered one of the most iconic moments in the history of the outdoor event.

The Penguins and Buffalo Sabres found themselves tied through regulation and overtime. It would take that dreaded shootout to decide this one.

Buffalo Ales Kotalik scored the first shootout attempt, but Conklin saved Buffalo’s second. Penguins defenseman Kris Letang scored, and Conklin stopped Buffalo again to set the scene.

As the snow fell upon the crowd at Ralph Wilson Stadium, all Crosby needed was a goal to win. He skated in, and smoothly slid the puck through Ryan Miller’s five-hole to win the game. This game set the standard for what has become one of the NHL’s best annual traditions.