The stage is set once again. After dispatching the Dallas Stars in five games, the Edmonton Oilers are back in the Stanley Cup Final, eager to rewrite the ending of last year’s heartbreak against the Florida Panthers.
With Connor McDavid and Leon Draisaitl leading the charge and the team holding home-ice advantage, the Oilers are hungry for redemption and for adding another title to their storied history.
As they chase what could be their first championship in over three decades, fans are once again asking, just how many times have the Oilers captured hockey’s greatest prize? Let’s take a walk down memory lane and relive the franchise’s golden years.
Edmonton Oilers Stanley Cup History
The Oilers are one of the most iconic teams in NHL history, especially known for their dominance in the 1980s. Since joining the NHL in 1979, the Oilers have won the Stanley Cup five times, a mark that ties them with the Pittsburgh Penguins for the sixth-most in league history.
TODAY 👏 IS 👏 THE 👏 DAY
The #StanleyCup Final rematch between the @FlaPanthers and @EdmontonOilers begins TONIGHT at 8p ET on @NHL_On_TNT, @SportsonMax, @Sportsnet, and @TVASports! pic.twitter.com/VCS5IF3JKy
— NHL (@NHL) June 4, 2025
The Oilers were originally founded in 1971 and played their first season in 1972-73 as a charter member of the World Hockey Association (WHA). After the WHA-NHL merger in 1979, Edmonton officially joined the NHL and began its climb to hockey greatness.
- 1983–84
vs. New York Islanders
Oilers won 4–1
First Cup win; ended Islanders’ 4-year reign - 1984–85
vs. Philadelphia Flyers
Oilers won 4–1
Back-to-back champions - 1986–87
vs. Philadelphia Flyers
Oilers won 4–3
Hard-fought 7-game victory - 1987–88
vs. Boston Bruins
Oilers won 4–0
Dominant sweep; Gretzky’s final Oilers Cup - 1989–90
vs. Boston Bruins
Oilers won 4–1
Fifth and most recent Stanley Cup win
The Oilers experienced a golden era almost immediately after joining the league. Led by legendary players such as Wayne Gretzky, Mark Messier, Jari Kurri, Paul Coffey, and Grant Fuhr, Edmonton quickly became a powerhouse.
They won their first Stanley Cup in 1984, ending the reign of the New York Islanders, who had won four straight championships. Edmonton beat them in five games, marking the start of a new dynasty.
Their second Cup followed quickly in 1985, and then two more in 1987 and 1988. Gretzky was at the center of all four victories, becoming the face of the franchise and a global ambassador for the sport. However, in 1988, after winning his fourth Stanley Cup with the Oilers, Gretzky was traded to the Los Angeles Kings in one of the most shocking moves in sports history.
Despite losing Gretzky, the Oilers won their fifth Stanley Cup in 1990, defeating the Boston Bruins in five games. This proved that the team still had enough talent and heart to compete at the highest level.
Since that 1990 victory, the Oilers have yet to win another Cup. They have had a few close calls, though, most notably in 2006, when they lost a hard-fought seven-game series to the Carolina Hurricanes in the Finals.
As of now, the five Stanley Cups in Oilers history rank behind only the Montreal Canadiens (24), Toronto Maple Leafs (13), Detroit Red Wings (11), Boston Bruins (6), and Chicago Blackhawks (6).
With stars like McDavid and Draisaitl leading the current generation, the Oilers are once again chasing history and hoping to end a championship drought that’s lasted more than three decades.
