Sidney Crosby turns 38: How many Stanley Cups had Wayne Gretzky and other NHL legends won at his age?

Sidney Crosby is once again making headlines on August 7, the day he celebrates his birthday. The Pittsburgh Penguins and NHL superstar turns 38 and remains one of the league’s biggest icons. Far from discussing retirement, the forward continues to prove he’s still got it, drawing comparisons to legendary figures like Wayne Gretzky.

To date, Crosby has hoisted the Stanley Cup three times (2009, 2016, 2017) and has received numerous prestigious individual honors, including the Conn Smythe, Art Ross, and Hart Trophies. He’s also been a key figure for Team Canada and is a member of the exclusive Triple Gold Club, thanks to his championships in the NHL, Olympics, and World Championships.

Debates about his legacy often place him among the top five players of all time, though comparisons to other greats continue. Age adds an interesting layer to the conversation, as Crosby, now 38, still wants to win, making him comparable to a historical star like Gretzky. It’s also worth looking at where players like Bobby Orr, Gordie Howe, and current star Alex Ovechkin stood at the same age.

How many Stanley Cups had Gretzky won by age 38?

Gretzky won all of his Stanley Cups with the Edmonton Oilers before turning 30, capturing four NHL championships between 1983 and 1988. After that, he never lifted the Cup again. He turned 38 in January 1999 and retired a few months later, in April of the same year.

Wayne Gretzky of the Edmonton Oilers after winning his first Stanley Cup by defeating the New York Islanders 4-1 in the series in 1984.

Crosby compared to Orr, Howe, and Ovechkin at age 38

Looking at the comparison, Crosby holds an edge over Bobby Orr, who had won 2 Stanley Cups with the Boston Bruins (1970 and 1972) by the time he was 38, although he actually retired early at age 30 and never added to that total.

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Gordie Howe, meanwhile, had claimed 4 Stanley Cups (1950, 1952, 1954, and 1955) with the Red Wings before turning 38, and didn’t win another during the rest of his lengthy career. As for modern stars, Ovechkin has just one Stanley Cup to his name by age 38, the historic 2018 title with the Washington Capitals, and has yet to add another since.