Bossy helped the Islanders win the Stanley Cup from 1980 to 1983, winning the Conn Smythe Trophy as playoff MVP in 1982. He scored the Cup-winning goals in 1982 and 1983 -- one of just two players
Returning in-season from back surgery to win the Stanley Cup. Beating cancer and winning the scoring title and MVP in the same season. Scoring 35 goals and 76 points in 43 games after retiring for
Gretzky and Co. picked up their third Stanley Cup in four years, knocking off Ron Hextall's Philadelphia Flyers. 2. Calgary Flames (1988-89) This time, they won the Cup -- the only one inWayne Gretzky has won a total of 4 Stanley Cups in four years, making himself a name. Here is the list below: 1983 – 1984 (Won the first Stanley Cup) 1984 – 1985 (Won the second Stanley Cup) 1986 – 1987 (Won the third Stanley Cup) 1987 – 1988 (Won the fourth Stanley Cup) Each of these cups was won while playing with the Edmonton Oilers. The Oilers are seeking their first Stanley Cup since 1990 after the blockbuster Wayne Gretzky trade. Edmonton last made the Stanley Cup Final in 2006, where they lost to the Carolina Hurricanes .