The countdown continues with the top hockey moments from the past 25 years. Make sure to check out moments 25 through 16 over here. This segment of the list starts to focus on the faces of the decade. Alexander Ovechkin, Connor McDavid, and Sidney Crosby appear a few times. So, let’s start with the early days of the Crosby era.
15: Detroit Red Wings vs Pittsburgh Penguins 2008 Stanley Cup Final Game 6 Ending
This series was a classic, pitting the past against the future. Specifically, the Detroit Red Wings were putting the finishing touches on a historic run while the Pittsburgh Penguins were the team on the rise. The Red Wings were the heavy favorites as Presidents’ Trophy winners and winners of three titles with their core. Yet, the Penguins gave them all they could handle with Sidney Crosby, Evgeni Malkin, and the young core proving they could compete with the best of them.
The Red Wings held a 3-1 lead in the final two minutes but the Penguins were fighting until the end. They scored a power play goal with the empty net to make it a one-goal game with 1:27 remaining. Then came the push in the final seconds, where Chris Osgood stopped a backhand shot by Sidney Crosby, and then the rebound was chipped through the crease by Marian Hossa and never crossed the goal line. Time ran out, and the Red Wings won their fourth Cup in 12 years.
14: Henrik Zetterberg’s Conn Smythe Shift
Speaking of the Penguins-Red Wings matchups, there were plenty of moments to choose from within those Finals series (you can probably have a top five just from those two). The other big one in the 2008 Final was the Henrik Zetterberg Conn Smythe shift, which, if you ask any Red Wings fan about, they’ll talk for hours about how significant the shift was, even though it didn’t result in a goal.
The situation was this. With a 2-1 Red Wings lead with just under 10 minutes to go in Game 4, the Penguins were given a 5-on-3 power play. So, Zetterberg was sent out to kill the penalty and did he ever. He blocked a shot from the point, prevented Crosby from scoring near the net on the rebound by tangling him up, then stole the puck on a cross-ice pass to kill more clock, and to wrap it up, prevented the Penguins from finding any open shots to get the Red Wings back to even strength.
The Red Wings ultimately won the game 2-1 to take a 3-1 series lead. Zetterberg was known throughout his career as a two-way player, and this shift embodied his defensive play. Better yet, he was the one who won the Conn Smythe Trophy after the Red Wings won it all with a great playoff run beyond just the shift.
13: Bruins-Maple Leafs 2013 First Round Game 7 Ending
Was this the great collapse of the era or the great comeback? It depends on who you ask. This game and how it ended were a preview of the decade to come, as the Boston Bruins and Toronto Maple Leafs would face each other multiple times in the First Round but every time, the Maple Leafs choked in Game 7 while the Bruins found a way to win.
This was the first version with the new era Maple Leafs, a team on the rise and entering a contention window, and the Bruins, a team that won the Cup in 2011 and was looking to add one more. The Maple Leafs boasted a 4-1 lead in the third period and a 4-2 lead with under two minutes to go. The star players on the Bruins stepped up when they needed them must with Nathan Horton starting the comeback, Milan Lucic cutting the deficit to one, and Patrice Bergeron not only tied the game but scored the overtime winner to end the series.
The Bruins would go on a run after this victory, losing in the Final to the Chicago Blackhawks. The Maple Leafs didn’t know that this would be a preview of things to come, as it took a decade for them to advance past the First Round after this collapse.
12: Alexander Ovechkin Hoisting The Cup
There’s something special when a generational superstar finally gets to hoist the Stanley Cup. For Alexander Ovechkin, his big moment was years in the making. He won every award and achieved every individual accolade possible. Yet, came up short in the playoffs with a Washington Capitals team that had a legacy of failure attached to it as well.
The 2018 playoff run was a sign that things were different. Most notably, the Capitals defeated the Pittsburgh Penguins in the Second Round, a team that always had their number in the playoffs. With back-to-back wins on the brink of elimination against the Tampa Bay Lightning in the Eastern Conference Final, the Capitals and Ovechkin punched their ticket to the Final. Most casual sports fans were rooting for the Vegas Golden Knights in the Final, the upstart team that made it in their inaugural season. Hockey fans, especially passionate ones, were rooting for the Capitals to win the Cup, especially since it meant Ovechkin would hoist it.
In the final seconds of Game 5, everyone watched the clock wind down, and Ovechkin was finally a champion. The hidden gem of this moment is Gary Bettman handing him the Conn Smythe Trophy first, which he gladly takes but shows minimal emotion while doing so. Then, the joy Ovechkin has as he lifts the Stanley Cup is unmatched and one of the moments that fans point to when thinking of his legacy in the NHL.
11: Sidney Crosby’s 2008 Winter Classic Shootout Goal
The idea of playing an NHL game outdoors once seemed like a dream. Players grow up skating on ponds or outdoor rinks as kids but to have a game in such an environment, much less a stadium, felt far-fetched. The NHL turned that dream into a reality when the Buffalo Sabres hosted the Pittsburgh Penguins in the 2008 Winter Classic at Ralph Wilson Stadium (now known as Highmark Stadium).
The game itself was a classic and better yet, lived up to the hype. The snow, the fans, and two great teams who wanted to prove this was their year. The game went into a shootout, and to win it, Sidney Crosby was called on for the final attempt. With a few moves on the slow ice, he snuck the puck past Ryan Miller for his first signature moment in a Hall of Fame career.
The big winner from this game was the NHL and hockey in general. The experiment proved to be a resounding success, and it’s why the league has at least one game in a different outdoor venue every year. But the first one needed a moment, and that’s what Crosby provided.
10: Auston Matthews 4-Goal Debut
It’s hard to find a debut better than the one Auston Matthews had. He entered the NHL with plenty of hype and was seen as the next great scorer who could turn the Toronto Maple Leafs into a perennial contender. Matthews wasted no time proving why he was an elite scorer.
The Ottawa Senators were a good team that season, a team that would reach the Eastern Conference Final that season. Yet, Matthews shredded their defense and goaltender Craig Anderson. His first goal came off a centering pass but his second came with him skating through the offensive zone and firing a sharp-angle shot past Anderson. Matthews started the second period where he left off the first but his third goal provided a glimpse into the future as he found open ice in the offensive zone and fired the puck into the back of the net, something he’d do throughout his NHL career.
Then came his fourth goal, which happened before the second period even expired. Matthews turned on the jets and took a William Nylander centering pass and deflected it into the net. Matthews became the first player to score four goals in an NHL debut, and it’s hard to see anyone having a more impressive start to a career than that.
9: Marc-Andre Fleury’s Save to end Game 7 of the 2009 Stanley Cup Final
In the rematch between the Detroit Red Wings and Pittsburgh Penguins, the Penguins got the last laugh. Fittingly, the situation mirrored the ending in the previous season. This time, the Red Wings were looking to put a finishing touch on their remarkable run with a Game 7 win at Joe Lewis Arena but trailed by one goal in the final seconds.
Then came the save. The puck was stopped in the traffic by the net, and then the puck slipped to Niklas Lidstrom with a wide-open net in front of him. Lidstrom took a last desperation slapper to tie the game but Marc-Andre Fleury, who was in no position to make the stop, came out of nowhere and put his body in front of the puck. By the time another skater touched it, the clock hit zero, and the Penguins won their first title of the Crosby, Fleury, and Malkin era.
The significance of the game also matters for this moment. At the time, this was a changing of the guard game as the Red Wings’ era of dominance was coming to a close, while the Penguins were starting theirs. This game kick-started the Hall of Fame careers of Crosby, Malkin, and the rest of the core but interestingly, this group had to wait another seven years before hoisting the Cup again.
8: TJ Oshie’s 2014 Olympic Shootout Performance
The gravity and weight of this game make the moment arguably the most iconic of the decade. The United States played Russia in the preliminary round but the game was in Sochi, Vladimir Putin was in the arena, and regulation wasn’t enough to determine the winner. That’s when a lesser-known forward on the St. Louis Blues became a household name.
After the first three rounds of the shootout, both coaches were allowed to select anyone to attempt a shot and use the same skater multiple times. For Russia, that meant turning to Ilya Kovalchuk and Pavel Datsyuk, two of the best shootout scorers in the game’s history. The USA turned to TJ Oshie for each attempt, and he went toe to toe with the greats. Better yet, he kept beating Sergei Bobrovsky with the same move over and over again to outduel the Russians.
This game was also a sign that the Russians weren’t ready for the Olympics, and it showed at the end of the day with a disappointing tournament. The USA didn’t have a great tournament either but Oshie’s name and his shootout performance still resonate even with casual sports fans.
7: Four-Nations Final: Connor McDavid’s Overtime Goal
The Four-Nations Faceoff not only lived up to the hype but far exceeded it to the point where the NHL has a hard time going back to the usual All-Star Game. The ending was ideal for this event as Canada and the USA battled in a 2-2 game that went into overtime, when there would be a golden goal scenario.
For Canada, this game meant more to the fans, the players, and the country, especially with their sovereignty under threat. They needed a hero who could take over the game and, when it mattered most, make the plays to win. Throughout the game, it was Jordan Binnington, who struggled earlier in the Four Nations but made the big stops throughout the game and in overtime.
In overtime, the goal came from the best player in the game, who had yet to have his moment on the big stage. Connor McDavid wasn’t the best player in the tournament (Nathan MacKinnon, interestingly enough, was named the MVP) but with Canada in need of a goal, he found open ice in the offensive zone and fired a one-timer past Connor Hellebuyck to win the game. The Final was another reminder that even though the USA team was great, when Canada needed their stars to step up, that’s what happened, and McDavid’s goal in some ways was a passing of the torch moment for the star player.
6: Alexander Ovechkin & Sidney Crosby’s Dueling Hat Tricks
As you’ve probably noticed, there are plenty of Crosby and Ovechkin moments on this list (including two more in store). It makes sense; they’ve been the two superstars of the past two decades and understandably have contributed to many of hockey’s iconic movements. That said, only a few moments involve both Crosby and Ovechkin.
On May 4, 2009, the two traded goals in the pinnacle of this player rivalry. The setting was Game 2 of the Eastern Conference Final, and the Capitals boasted a 1-0 series lead. Crosby scored the first goal of the game but Ovechkin quickly responded, and the battle was on. The fascination is how both players scored throughout the game. Crosby scored with battles near the net, collecting loose pucks and finishing chances to earn his hat trick. Ovechkin did it with his shot, sometimes from “Ovi’s Office,” and his third goal came on a rush where he wristed the puck past Marc-Andre Fleury’s glove.
The Capitals won the battle 4-3 and took a 2-0 series lead. But the Penguins won the war as they won four of the next five games to take the series in seven games. Hockey isn’t built on player rivalries, and there are few in the NHL. However, Crosby and Ovechkin had plenty of battles, and this was, without question, the best.
