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 face off on Saturday before facing off again on Sunday. With Ovechkin in the final year of his contract and undecided about his future, the second half of the home-and-home game could also be the last time fans get to witness one of the greatest individual rivalries hockey has ever known.

In 2005-06, the NHL was coming off a year of lockout and desperately needed something to restore the league’s relevance on the national stage. As luck would have it, Crosby and Ovechkin would both take the ice for their rookie seasons with the Pittsburgh Penguins and Washington Capitals respectively, sparking an epic rivalry that now spans two decades.

The two young superstars immediately lived up to expectations, totaling 91 goals and 208 points during the 2005-06 campaign. Ovechkin beat Crosby for the Calder Trophy, but Crosby scored his fair share of shots in the 20 years since.

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Over the years, the two living legends have rewritten the history books, racked up awards, met four times in the playoffs and won the Stanley Cup together four times. It’s been an incredible journey for two players who have a strong case to be among the top 10 players of all time.

Ovechkin is now the undisputed goal-scoring king, and Crosby has been a magician of the three-zone game throughout his career. They took 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 rank among the greatest on the ice in every statistical category.

In their previous 99 meetings, Crosby has the edge in wins (56-43), assists (79-50) and points (127-103). However, as was entirely fitting, Ovechkin outscored Crosby, 53-48.

As Crosby and Ovechkin prepare to face off for the 100th (and perhaps final) time, let’s not dwell on the idea that this great rivalry might be coming to an end – or how old that makes us feel. Instead, let’s look back at the best moments of the two greatest players of their generation.

Best moments between Ovechkin and Crosby

5. Weekend All-Star Team

After 18 years of facing each other, 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 just be hate all the time, right? There must be moments of respect and admiration for each other’s achievements. This has happened more often in recent years, including Crosby and Penguins teammate Evgeni Malkin gifting Ovechkin a Rolex for breaking Wayne Gretzky’s goalscoring record. The moment above truly marked the thaw of their relationship in the later years of their career.

4. Ovi vs. Crosby: Episode 1

On November 22, 2005, Crosby and Ovechkin met on the ice for the very first time, and they did not disappoint. Crosby’s Penguins won the game 5-4, and he was the more productive player, but both put on the spectacle. Crosby scored a great goal when he split the Capitals defense and fired a backhand shot that created a popping bottle that you don’t see in today’s game. Crosby also added a stylish assist from a knee.

Ovechkin had a nice assist on a Matt Pettinger goal, but he could have had a much more important game. Ovechkin walked Penguins defenseman Ryan Whitney with a brilliant move, but the post and goaltender Sébastien 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 took place 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 half and led Pittsburgh to an emphatic 6-2 victory with two goals and an assist. Crosby would go on to win his first of three Stanley Cup rings that year.

Ovechkin scored for the Capitals, but it was an overall disappointing performance that foreshadowed what this playoff rivalry would look like for many years to come.

2. Ovechkin and the Capitals finally break through

In 2018, Ovechkin and the Capitals lost three straight playoff series to Crosby and the Penguins, including back-to-back losses in 2016 and 2017. What made the two most recent losses particularly painful was that Pittsburgh won the Cup in each of the previous two playoff series.

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 that for once, the story ended differently. Game 6 was a close control game and the teams went to overtime tied at 1-1. Crosby had assisted on the Penguins’ lone goal, and Ovechkin was yet to get on the scoresheet.

Then, in overtime, Ovechkin threw teammate Evgeny Kuznetsov on a breakaway to score the winning goal. Washington slayed the dragon and won the first Stanley Cup in franchise history.

1. Dueling hat tricks

Hands down, the most memorable moment of 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 third-period goals, including the eventual game-winner.

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

Crosby completed his hat trick by pulling Pittsburgh to within one with 30 seconds left, but he couldn’t find a fourth to tie the game. He just had to settle for a possible series win and the Stanley Cup – not a bad consolation prize.