Sidney Crosby vs. Alex Ovechkin: Top moments as the rivals meet for the 100th time

For the 100th and potentially final time in their careers — including the playoffs — Sidney Crosby and Alex Ovechkin will go head-to-head on Saturday before facing off again on Sunday. With Ovechkin on the final year of his contract and undecided about his future, the second half of the home-and-home may also be the final time fans get to witness one of the greatest individual rivalries hockey has ever seen.

In 2005-06, the NHL was coming out of a lockout year and desperately needed something to make the league relevant on the national stage again. As luck would have it, Crosby and Ovechkin would both take the ice for their rookie seasons for the Pittsburgh Penguins and Washington Capitals, respectively, sparking an epic rivalry that has now spanned two decades.

The two young superstars immediately delivered on the hype, combining for 91 goals and 208 points in that 2005-06 campaign. Ovechkin beat out Crosby for the Calder Trophy, but Crosby would score his fair share of blows in the 20 years that followed.

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Throughout the years, the two living legends have rewritten the history books, racked up awards, met in the playoffs four times and combined to win the Stanley Cup four times. It’s been an incredible run for two players who have strong arguments to be among the top 10 players of all-time.

Ovechkin is now the undisputed goal-scoring king, and Crosby has been a playmaking wizard in all three zones throughout his career. They’ve taken different paths to reach their respective places in hockey history, but longevity is a trait they share in common, and it has allowed Crosby and Ovechkin to land among the greatest to take the ice in every statistical category.

In their previous 99 head-to-head matchups, Crosby has the edge in wins (56-43), assists (79-50) and points (127-103). However, as is only appropriate, Ovechkin has Crosby beaten in goals, 53-48.

As Crosby and Ovechkin get set to do battle for the 100th (and possibly final) time, let’s not dwell on the idea that this great rivalry may be coming to an end — or how old that makes us feel. Instead, let’s look back at the best moments from the two greatest players of their generation.

Top Ovechkin vs. Crosby moments

5. All-Star weekend team-up

After 18 years of being pitted against one another, Crosby and Ovechkin teamed up for a more heartfelt moment at the 2023 All-Star Skills Competition. The rivals took the ice together and helped Ovechkin’s son, Sergei, beat Roberto Luongo on a breakaway.

Rivalries can’t be all hatred all the time, right? There have to be moments of respect and admiration for one another’s accomplishments. That’s happened more often in recent years, including Crosby and Penguins teammate Evgeni Malkin gifting Ovechkin a Rolex for breaking Wayne Gretzky’s goal record. The moment above just really signaled the thawing of their relationship in the latter years of their careers.

4. Ovi vs. Crosby: Episode 1

On Nov. 22, 2005, Crosby and Ovechkin met on the ice for the very first time, and they didn’t disappoint. Crosby’s Penguins won the game 5-4, and he was the more productive player, but both of them put on a show. Crosby scored a gorgeous goal when he split the Capitals’ defense and roofed a backhand shot that created a bottle pop you no longer see in today’s game. Crosby also added a stylish spin-o-rama assist from one knee.

Ovechkin tallied a nice assist on a goal by Matt Pettinger, but he could’ve had a much bigger game. Ovechkin walked Penguins defenseman Ryan Whitney with a brilliant move, but the post and goaltender Sebastien Caron combined to keep the puck out of the net.

3. Crosby strikes first in the playoffs

The first of many playoff battles between Crosby and Ovechkin occurred in 2009, and as always, it was a long series. In Game 7, Crosby simply took over. He opened the scoring midway through the first period, and he led Pittsburgh to an emphatic 6-2 victory with two goals and one assist. Crosby would go on to capture his first of three Stanley Cup rings that year.

Ovechkin did score for the Capitals, but it was an overall disappointing performance that foreshadowed what this rivalry would look like in the postseason for many years.

2. Ovechkin, Capitals finally break through

In 2018, Ovechkin and the Capitals had lost three consecutive playoff series to Crosby and the Penguins, including back-to-back defeats in 2016 and 2017. What made the two most recent defeats especially painful was that Pittsburgh had gone on to win the Cup in each of the previous two postseasons.

So, when Game 6 of the second-round series rolled around in 2018, everyone knew the Penguins would force a Game 7 and break the Capitals’ hearts. Except, for once, the story ended differently. Game 6 was a tight checking game, and the teams went to overtime tied at 1-1. Crosby had assisted on the Penguins’ lone goal, and Ovechkin hadn’t gotten on the scoresheet yet.

Then, in overtime, Ovechkin sprung teammate Evgeny Kuznetsov on a breakaway for the game-winning goal. Washington slayed the dragon and went on to win the first Stanley Cup in franchise history.

1. Dueling hat tricks

Hands down, the most memorable moment in this rivalry came in Game 2 of that 2009 playoff series. Crosby and Ovechkin traded the first three goals of the game, with Crosby giving the Penguins a 2-1 lead in the second period. Ovechkin responded with two goals in the third period, including the eventual game-winner. 

Ovechkin’s hat-trick goal was a missile at the top of the circles that plunged the Verizon Center into chaos.

Crosby notched his hat trick as he pulled Pittsburgh within one with 30 seconds left, but he couldn’t find a fourth to tie the game. He just had to settle for an eventual series win and Stanley Cup — not a bad consolation prize.