Five Stanley Cups He is most remembered for his time with the Edmonton Oilers, with whom he spent the majority of his career and won five Stanley Cups: in 1984, 1985, 1987, 1988, and 1990. During that period he was a part of three all-star games (1982, 1983, and 1989). He currently holds several NHL records including most goals by a right winger in one season (69 in 1982-83). After his retirement from playing, he became an assistant coach with the New York Rangers, Chicago Blackhawks, and Boston Bruins before being named head coach of the Tampa Bay Lightning in 1999. He remained in this position until 2001 when he was replaced by Jon Gruden. After two seasons out of coaching, he returned to the Lightning as an assistant coach under Rick Tocchet during the 2004-05 season. In 2006, he rejoined the Blackhawks as an assistant coach under Joel Quenneville. He left this position after one season to become head coach of the Calgary Flames but was fired after the 2008-09 season. Gregg returned to Tampa Bay as an assistant coach under Guy Boucher in 2009 and remains in this position today. He has been nominated for the Masterton Trophy which is given to the player who demonstrates great skill at keeping himself healthy while other players around him are injured.