How many Stanley Cups did Wayne Gretzky win? He won four Stanley Cups. All four championships came with the Edmonton Oilers, during the team’s extraordinary run in the 1980s.
Gretzky lifted the Cup in 1984, 1985, 1987, and 1988. The Oilers defeated the New York Islanders in the 1984 Final, then repeated against the Philadelphia Flyers in 1985. They returned to the top in 1987 against the Flyers and won again in 1988 against the Boston Bruins.
Gretzky was named the Conn Smythe Trophy winner as playoff MVP in 1985 and 1988. A common mix-up is assuming he won a championship with the Los Angeles Kings because he helped take them to the 1993 Stanley Cup Final. The Kings lost that series to the Montreal Canadiens, so Gretzky finished his career with four championships.