How many times did Wayne Gretzky make the Stanley Cup? (2024)

Wayne Gretzky is widely considered one of the greatest hockey players of all time. During his 20-year NHL career, spanning from 1979 to 1999, Gretzky set numerous records and led his teams to several Stanley Cup victories.

Quick Answer

Wayne Gretzky made the Stanley Cup four times over the course of his NHL career. He won the Stanley Cup with the Edmonton Oilers in 1984, 1985, 1987 and 1988.

Gretzky’s NHL Career

Wayne Gretzky began his NHL career with the Edmonton Oilers in 1979 after signing with the WHA’s Indianapolis Racers at age 17. He quickly became a standout player, winning the Hart Trophy for NHL MVP in his first season and leading the Oilers to several playoff appearances in the early 1980s.

In the 1983-84 season, Gretzky led the Oilers to their first Stanley Cup championship, defeating the New York Islanders. He recorded over 200 points in the regular season and tallied 43 points in 19 playoff games, winning the Conn Smythe Trophy for playoff MVP.

The following year, Gretzky and the Oilers won the Cup again, sweeping the final series against the Philadelphia Flyers. Gretzky dominated with 47 points in 18 playoff games, once again taking home the Conn Smythe.

After a third-place finish in 1986, Gretzky captained the Oilers to another Cup victory in 1987, defeating the Flyers in seven games. He recorded 183 regular season points and then notched 34 points in 21 playoff games to win his third Conn Smythe.

In 1988, the Oilers won their fourth championship in five years by defeating the Boston Bruins in the final. Gretzky put up 149 regular season points and 31 more in the playoffs to capture an unprecedented fourth Conn Smythe Trophy.

Later Career and Retirement

Prior to the 1988-89 season, Gretzky was shockingly traded to the Los Angeles Kings. He led the Kings to the 1993 Stanley Cup Finals but lost to the Montreal Canadiens. Despite another Finals appearance in 1993 with the Kings, Gretzky was unable to capture a fifth championship.

In 1996, Gretzky signed with the St. Louis Blues but was eliminated in the playoffs. He was then traded to the New York Rangers in 1997 and helped lead them to the conference finals in 1997, but could not reach the Finals again before retiring in 1999.

So while Gretzky made a huge impact throughout his NHL career, winning nine Hart Trophies and 10 scoring titles, his Stanley Cup success was limited to those four championships with the Oilers dynasty of the 1980s. He reached the Finals one other time in 1993 with the Kings but did not win another Cup.

Gretzky’s Stanley Cup Championships

Here is a summary of the four Stanley Cup championships Wayne Gretzky won during his NHL career:

As the table shows, Gretzky won the Cup four times – all with the powerhouse Oilers of the 1980s. He defeated the Islanders, Flyers, and Bruins in those championship seasons and dominated with his offensive production, averaging nearly 40 points per playoff run.

Gretzky’s Stanley Cup Success in Context

Gretzky’s four Stanley Cups place him among the sport’s all-time great champions. Here is how Gretzky compares to some other NHL legends:

• Henri Richard – 11 Stanley Cup wins (most all-time)
• Jean Beliveau – 10 Stanley Cup wins
• Yvan Cournoyer – 10 Stanley Cup wins
• Maurice “Rocket” Richard – 8 Stanley Cup wins
• Wayne Gretzky – 4 Stanley Cup wins
• Gordie Howe – 4 Stanley Cup wins
• Mario Lemieux – 2 Stanley Cup wins
• Steve Yzerman – 3 Stanley Cup wins

While Gretzky’s four championships lag behind record-holders like Henri Richard and Jean Beliveau, who played for the powerhouse 1950s-60s Montreal Canadiens, he is still tied with Gordie Howe for the fourth most Cups won by an individual player. Only a handful of players in NHL history have won more than four as part of hockey’s greatest dynasties.

Gretzky also ranks above contemporary legends like Mario Lemieux and Steve Yzerman who captained their teams to multiple Cups in the 1990s and 2000s but did not surpass the four that Gretzky captured.

Gretzky’s Impact on the Oilers’ Stanley Cup Years

While hockey is a team sport, Wayne Gretzky’s individual brilliance played a massive role in leading the Oilers to their four championships:

• He won the Art Ross Trophy as the NHL’s leading scorer in each of the Oilers’ Cup-winning seasons
• He took home the Hart Trophy for league MVP in the 1984, 1985, and 1988 seasons
• He broke the 200-point mark twice during the Oilers’ championship runs (1983-84 and 1984-85)
• He recorded over 40 playoff points in the 1984 and 1985 postseasons
• He was awarded the Conn Smythe Trophy for playoff MVP in all four Cup years

Without Gretzky’s consistent and extraordinary offensive production, it’s very unlikely the Oilers would have achieved such a level of dominance. His scoring prowess lifted up the team during the regular season and playoffs. He simply controlled games in a way that few other players in history have matched.

Of course, Gretzky did not win alone. The Oilers teams featured other Hall of Famers like Mark Messier, Jari Kurri, Paul Coffey and Grant Fuhr who all played key roles. But Gretzky unquestionably spearheaded those championship squads and his presence on the ice tilted the ice in the Oilers’ favor against any opponent.

Conclusion

Wayne Gretzky reached hockey’s ultimate prize four times over the course of his illustrious career. He won the Stanley Cup in four out of five seasons between 1984 and 1988 as the centerpiece of the Edmonton Oilers dynasty. Gretzky’s record-breaking scoring feats powered those championship teams and he rightfully earned the Conn Smythe Trophy in each victorious campaign. While Gretzky fell short of winning a fifth Cup after leaving Edmonton, his four titles place him among the very top tier of NHL champions.