As head coach of the Oilers, he won 89 playoff games and lost 37 en route to four Stanley Cups in five Finals appearances. Stanley Cup champion as head coach: 1984, 1985, 1987, 1988. Edmonton Oilers. Stanley Cup champion as president and general manager: 1984, 1985, 1987, 1988, 1990. Edmonton Oilers. Stanley Cups: 0: Conference championships: 0: (Gretzky's agent for over 20 years), (who eventually went on to win the Cup that year) in game five of a 4–1 A.Ovechkin led his team to the 2018 Stanley Cup championship. He contributed his 15 goals in the Stanley Cup and won the Conn Smythe Trophy for being the MVP in the 2018 playoffs. Q. How many Stanley Cups did Gretzky win? Winning 4 Stanley Cups , Gretzky set records in both regular season and post-season play, holding the record for most career regular season goals (894), assists (1,963), points (2,857) and hat-tricks (50). The Capitals were eventually defeated by Pittsburgh, the eventual Stanley Cup champions, in seven games. Ovechkin finished the 2009 playoffs with a postseason career-high 21 points in 14 games. He went on to win the Hart and Pearson trophies for the second consecutive year, becoming the seventeenth player to win the Hart multiple times. 125. Question: How many Stanley Cup wins has Wayne Gretzky had during his career? Answer: Four. 126. Question: How many Stanley Cup championships did Mario Lemieux win as a player? Answer: Two. 127. Question: Which former NHL team won their first-ever Stanley Cup in 1906? Answer: Montreal Wanderers. 128. On Oct. 11, 1984, in his first game, on his first shift, on his first shot, he notched his first goal. No. 66 (Gretzky's No. 99 turned upside down) went on to win Rookie of the Year, scoring 100 Scores. Schedule. Standings. Stats. Teams. Daily Lines. How To Watch NHL Games. More. We go inside the eye-popping numbers to explain how the best player in the world has gotten even better this CJDB.