Gregg received a contract offer from the New York Rangers but rejected it to spend the year with David Bauer and the Canadian national team,[1] and captained Canada's entry at the 1980 Winter Olympics in Lake Placid.

He was at last convinced to accept an NHL offer by his hometown Edmonton Oilers, and joined the team for the 1982 playoffs, appearing in four games.

Receiving as much notoriety from the fact that he had a medical degree as he did for his solid play on the blueline, he helped the Oilers reach the Stanley Cup finals in 1983.

[3] Gregg retired after the Oilers' disappointing loss in the 1986 playoffs but returned to the team six weeks into the season and helped Edmonton win their third championship in 1986–87.

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

[10] The Dr. Randy Gregg Award is presented annually by Canadian Interuniversity Sport (CIS) to reward excellence in the student-athlete.