The Stanley Cup The Stanley Cup is a trophy awarded annually to the playoff champion club of the National Hockey League (NHL) ice hockey league. It was donated by the Governor General of Canada Lord Stanley of Preston in 1892, and is the oldest professional sports trophy in North America. Inscribed the Dominion Hockey Challenge Cup, the trophy was first awarded to Canada's amateur ice hockey The Kings’ Wayne Gretzky was held off the score sheet and the Canadiens cruised to a 4-1 win and their 24th Stanley Cup. Photo by FRANK GUNN / Canadian Press Irvin agrees the Quebec series was 9. Most Goals in a Season (92) In the 1981-82 season, Gretzky broke Phil Esposito’s record for goals in a season by amassing 92 over 80 games. Based on the numbers that today’s superstars put Connor McDavid asked Wayne Gretzky what it's like to win the Stanley Cup in Edmonton during an interview they did together for GQ Sports. Gretzky's answer to the Edmonton Oilers captain included a Wayne Gretzky won the award a record nine times during his career, including eight in a row from 1980-87. Gretzky and his Edmonton Oilers teammate Mark Messier are the only players to win the Hart The first Stanley Cup won by Wayne Gretzky was in 1983/84. Wayne Gretzky was the captain of the Edmonton Oilers during their 1984 Stanley Cup win. Their fifth season in the National Hockey League. The Boston Bruins were defeated by the Edmonton Oilers 5-4 in game seven of the finals. Wayne Gretzky has won a total of 4 Stanley cups. in 1984, 1985, 1987 and 1988, all of which playing with the Edmonton Oilers. Gretzky also won the Conn Smythe trophy twice in 1985 and 1988, won Hart trophy 9 total times from 1980 all the way to 1987 and in 1989, oh and he also snagged the Art Ross trophy a total of 10 times. What year did Wayne gretzky win his first Stanley cup? Gretzky helped the Edmonton Oilers win the Stanley Cup in 1984, 1985, 1987, and 1988.The great Gretzeky won 4 Stanley cups. How many world championships did Wayne Gretzky win as a senior? After two non-playoff seasons with the Los Angeles Kings, and a mid-season trade to the St. Louis Blues in the 1995-96 season, Gretzky became one of the few athletes to take less money to play in Edmonton would also win another Stanley Cup that year, a victory that came almost two years after star player Wayne Gretzky was traded away. Related Stories. From 1988: The day Wayne Gretzky went BEI1.