 He retired from professional hockey again for the 1987–88 campaign to enter a residency program in orthopedic surgery as well as represent Canada at the 1988 Winter Olympics, but re-joined Edmonton for the playoffs to win another Stanley Cup.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.