How Many Stanley Cups Has Sidney Crosby Won?

Sidney Crosby has won three Stanley Cups during his long career with the Pittsburgh Penguins. He won his first in 2009, and then won back-to-back Stanley Cups in 2016 and 2017.

Before making the NHL, Sidney Crosby was a highly touted prospect and many thought he would become a superstar. Well, he not only lived up to these expectations, but surpassed them as he is already a top 15 scorer in NHL history, and isn’t done yet.

But how many Stanley Cups has Crosby been able to win in his Hall of Fame career? Keep reading to find out.

Key Takeaways

  • During his career so far, Sidney Crosby has won three Stanley Cups, which is currently tied for the most by any active NHL player.
  • He won his first Stanley Cup in 2009, and became the youngest NHL captain to win a Stanley Cup, at only 21 years old.
  • His next two Stanley Cups would come back-to-back in 2016 and 2017, and Crosby ended up winning the Conn Smythe trophy both times as the player most valuable to his team in the playoffs.

2009 Stanley Cup

Sidney Crosby took home his first Stanley Cup in 2009, which was only a few seasons after he was drafted. The Pittsburgh Penguins got into the playoffs with a 45-28-9 record, which was good enough for 4th in the Eastern Conference.

Despite only playing 77 games in the regular season, Crosby scored 33 goals and got 70 assists to propel his team into the playoffs. Once in the playoffs, the team defeated the Philadelphia Flyers, Washington Capitals, and Carolina Hurricanes to reach the finals.

In the finals, they would face off against the Detroit Red Wings, who were the second seed in the Western Conference. The series would go seven games with the Penguins winning the final game and thus winning the Stanley Cup.

Crosby and the Penguins also got some revenge by winning this series, as it was a rematch of the Stanley Cup Finals from the previous season, which was won by the Detroit Red Wings in six games.

Crosby was a major reason for the success of the Penguins in the playoffs, as he scored 31 points in only 24 playoff games. Sidney Crosby was only 21 years old when the Penguins won the Stanley Cup, which made him the youngest captain to win a Stanley Cup in league history.

2016 Stanley Cup

His next Stanley Cup would come in 2016. The Penguins made the playoffs each year from 2009 to 2016, but weren’t able to take the final step until this year. In the regular season, the Penguins were the second seed with a record of 48-26-8.

Crosby led the team with 85 points in 80 games, and the team made a lot of important additions this season to bolster their team, including bringing on Phil Kessel, Nick Bonino, Trevor Daley, and many others.

In the playoffs, the team would have a tough road to the finals, but would ultimately move past the New York Rangers, Washington Capitals, and the Tampa Bay Lightning. In the finals, they would match up against the San Jose Sharks, who were making their first ever appearance.

The Penguins would go on to beat the Sharks in six games, and Crosby would win his second Stanley Cup and also take home his first ever Conn Smythe Trophy as MVP of the playoffs.

2017 Stanley Cup

He wouldn’t need to wait long for his next and final Stanley Cup, as it would come in the following season. Like their last season, the Penguins would finish the regular season as the second seed, this time with a record of 50-21-11.

Crosby would again lead the team in scoring as he had 89 points in only 75 games, and scored the most goals in the league with 44. The team was largely the same as the previous season, though the team did bring on defensemen Ron Hainsey and Mark Streit at the trade deadline.

On their journey to the Stanley Cup Finals, the Penguins would defeat the Columbus Blue Jackets, Washington Capitals, and Ottawa Senators. Two of those three series went to seven games, so the Penguins didn’t have a simple path to the Stanley Cup Finals.

In the final, they would go up against the Nashville Predators, who were making their first-ever Stanley Cup Finals appearance. The Penguins would end up winning in six games, shutting the Predators out in the final two games of the series.

Not only did Crosby win his second-straight Stanley Cup, but also won another Conn Smythe Trophy in back-to-back seasons, making him one of only a few players to achieve this.


Here are a few commonly asked questions about Sidney Crosby and his performance in the playoffs and Stanley Cup Finals, along with their answers.

How many points has Crosby scored in the playoffs?

During his career, Sidney Crosby has scored 71 goals and 130 assists for 201 points in 180 playoff games. This is good for 6th all-time, and with him still being an active player, this number could grow.

How many times has Crosby appeared in the Stanley Cup Finals?

Sidney Crosby has appeared in the Stanley Cup Finals on four separate occasions. He won three of them, and his only loss in the finals came in 2008, when the Penguins lost to the Detroit Red Wings in six games.

Final Thoughts

Throughout his near 20-year career (as of 2023), Sidney Crosby has won three Stanley Cups, including two back-to-back in 2016 and 2017. He has been one of the biggest superstars of the 21st century in the NHL and is a surefire Hall of Famer when he eventually retires.

Is there anything else that you feel I should have mentioned in this article? If so, don’t forget to let me know in a comment.

About Kale
Being from Canada, hockey is essentially a way of life. I instantly fell in love with the game since I was being put on skates. From playing as a child (and the occasional street hockey game with friends today) to being a fan for over 20 years, I’m here to share my knowledge and passion for hockey. Email:

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