2 days ago · In a mild upset, Messier beat his teammate Wayne Gretzky to win a Conn Smythe. Both guys contributed a ton in Edmonton’s first Cup run, but Messier got the nod. In addition to scoring 26 points A four-time Stanley Cup champion, he captured the greatest trophy in sports in 1984, 1985, 1987 and 1988 with the Edmonton Oilers. 2. Gretzky was a two-time Conn Smythe Trophy winner in 1985 and 1988. Q: Did Gretzky win any championships during his career? A: Yes, Gretzky won four Stanley Cup championships with the Edmonton Oilers in 1984, 1985, 1987, and 1988. Q: How many points did Gretzky score during his career? A: Gretzky scored a total of 2,857 points during his career, making him the all-time leading scorer in the National Hockey League. With the LA Kings, did Gretzky win a Stanley Cup? Gretzky started skating at the age of two and a half, and his father was his first coach. Gretzky led the Oilers to four Stanley Cup wins as a center and team captain (in 1983–84, 1984–85, 1986–87, and 1987–88). He was dealt to the Los Angeles Kings after the 1987–88 season. The team went 2–3–0 under Tocchet. Gretzky eventually resumed his duties on December 28. Tocchet and the Penguins celebrating their 2017 Stanley Cup win in Nashville. Tocchet was named as the associate coach of the Tampa Bay Lightning on July 9, 2008. 2TaN.