How many Stanley Cups has Sidney Crosby won?

Sidney Crosby entered the NHL in the 2005-06 season with the nickname ‘Sid the Kid’. Well ‘The Kid’ has grown up and won almost everything you could possibly win. But, how has he done in winning hockey’s ultimate prize? 

How many Stanley Cups has Sidney Crosby won? Sidney Crosby has won three Stanley Cups all with the Pittsburgh Penguins. His first cup win came in 2008-09 and then back-to-back wins in the 2015-16 and 2016-17 seasons.

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It comes as no surprise that he was integral in each of three cup wins. Let’s take a closer look at each of those Stanley Cups and how Sidney performed in each. 

Stanley Cup #1 2008-09 Pittsburgh Penguins vs Detroit Red Wings – Penguins in 7 games


What happened?

A couple of things make this Stanley Cup quite memorable. It was a rematch of the previous years Stanley Cup finals, which the Wings won in 6 games. 

As we look back this was also a passing of the torch as the Red Wings dominance of the ‘90 and early 2000s was coming to an end and now it was the Penguins and Sid who were taking the spotlight. 

As the series progressed it looked like the Wings were going to take it again. The series had been tied 2-2 when Detroit crushed Pittsburgh in game 5 by a score of 5-0. It like all but inevitable that Detroit would win one more game and capture yet another Stanley Cup.

However, Pittsburgh grinded out a tight defensive battle in Game 6 by a score of 2-1 to force a Game 7 back in Detroit. 

Pittsburgh stuck to the same formula in Game 7 with a tight defensive game. Bolstered by an amazing performance by Marc-Andre Fleury who made a number of key stops in the last few minutes of the game the Pens claimed the Stanley Cup by winning 2-1. 

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How did Sidney do?

Sidney had a strong playoffs, but it was Pittsburgh’s other superstar, Evgeni Malkin, who won the Conn Smythe trophy as Most Valuable Player. 

Sidney would draw the other team’s best defensive players in the playoffs, which would allow Malkin more room to play against weaker players and dominate. It must be amazing to have two superstars on a team like that!


Sidney Stat Line for the Finals

Games: 7 Goals: 1 Assits: 2 Points: 3



Stanley Cup # 2 2015-16 Pittsburgh Penguins vs. San Jose Sharks – Penguins in 6 games



What happened?

Nobody thought it would take 6 years for the Penguins to get back to the Stanley Cup after Crosby and company won their first. 

However, after several disappointing playoff results in the subsequent years Pittsburgh put it all together to make it to the finals. This time though they came in as the favourites against the San Jose Sharks. 

The series was over in 6 games against a veteran Sharks team who had their own playoff disappointments up to this point. 

When looking back at the stats of the series it makes it seem like the series was closer than it was, but the actual playing out of the games had Pittsburgh in control for the whole series. It never seemed in doubt that the Penguins were going to win their second cup in the Sidney era. 

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How did Sid do?

Well, if Sidney played second fiddle to Malkin in his first Stanley Cup run there was no question of who was the star in this run. Sidney Crosby dominated the whole playoffs including the finals. 

This may have been Crosby’s best playoffs of his career as he was dominant in all of his series. Crosby may never put up all of the points that a Gretzky or Lemieux did in their runs to the cup finals, because Crosby is a different type of player. Crosby is known as arguably the best all-around player.

For those efforts Sid was awarded with his first Conn Smythe trophy. 


Sidney Stat Line for the Finals 

Games: 6 Goals: 0 Assits: 4 Points: 4


Stanley Cup #3 2016-17 Pittsburgh Penguins vs Nashville Predators – Penguins in 6 


What happened?

Due to the long NHL seasons and playoffs it is almost unheard of for a team to win back-to-back Stanley Cups. But, this is exactly the position that the Penguins found themselves in. 

During the season and at the start of the playoffs it was actual Pittsburgh’s rival the Washigton Capitals who were favoured for the cup. However, Pittsburgh knocked them out in a great second round series in 7 games. The Pens would play another 7 game series against the Senators in the Eastern Conference Finals before they met up with the Preds, who were in their first Stanley Cup Finals. 

Much like the San Jose series the previous year, the outcome never really seemed in doubt. The Preds kept it close, but watching the series you always felt this was going to be Pittsburgh’s cup, again. 

Pittsburgh with all of their experience just knew how to win the big games and it always came through when they needed it. 

The Penguins won for the second year in a row in their opponent’s arena in the 6th game. 

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How did Sid do?

Well, Sid did something in this series that only two others (Bernie Parent and Mario Lemieux) have ever done. He won back-to-back Conn Smythe awards as Most Valuable Player in the playoffs. 

Again, Crosby will not dazzle you with mind-blowing stats, but it is undeniable that he is the heart and soul of that team. He sets the standard of the Penguins play with an amazing intensity and attention to detail that translate into an amazing all around performance and, most importantly, wins! 


Sidney Stat Line for the Finals

Games: 6 Goals: 1 Assits: 6 Points: 7


How does 3 Stanley Cups compare with other all-time greats? 


Gretzky won 4 and Lemieux won 2, so three Stanley Cups is up there with the other greats. 

In this day in age with the business of hockey it is very difficult to construct a team and keep it together that can win multiple Stanley Cups. 

So to win three in your career is a pretty amazing accomplishment. 

As well, I think it is quite impressive that Sidney was able to win a Stanley Cup so early in his career – in only his 4th year. 

What may have been a little surprising is that Sidney didn’t win another one very soon after. As the years went by people started to wonder if he would ever win another Stanley Cup, but the back-to-back Stanley Cups put to bed any question of Sid’s place as one of the greatest of the game. 

Like the other greats who have gone before him, Sid has won everything you can win in hockey, but it is the Stanley Cups he will cherish the most!

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