Wayne Gretzky Stanley Cups: How Many Stanley Cups Did Wayne Gretzky Win? Wayne Gretzky emerged victorious in a total of four Stanley Cup championships. His remarkable journey with the Edmonton Oilers led to triumphs in the years 1983-84, 1984-85, 1986-87, and 1987-88. Notably, during two of these memorable campaigns, he earned the esteemed Conn Smythe trophy, solidifying his … [Read more...] about Wayne Gretzky Stanley Cups: How Many Stanley Cups Did Wayne Gretzky Win?