Gregg spent two more years with the Oilers as a solid depth defender, helping the team win their fifth Stanley Cup in seven years in 1990. He was one of seven players to play for all five championship teams. Exposed in the NHL Waiver Draft in 1990, he was claimed by the Vancouver Canucks but decided again to retire. However, after a year away from the sport, he signed with the Canucks for the 1991–92 campaign, appearing in 21 games and providing valued veteran leadership for a young improving team, before retiring for good following the season.