Randy Gregg Randall John Gregg ( born February 19 , 1956 in Edmonton , Alberta , Canada ) is a retired professional defenceman who spent 10 seasons in the National Hockey League and is currently a family physician in Edmonton . He is best known for his time with the Edmonton Oilers , where he spent most of his career and won five Stanley Cup s 1984 , 1985 , 1987 , 1988 , 1990 . Playing career . Gregg attended the University of Alberta to work toward a medical degree , and playing hockey was a secondary priority . However , he became one of the top players in Canadian university hockey , leading the Golden Bears to two CIAU championships , and was CIAU Player of the Year in 1979 . He received a contract offer from the New York Rangers but rejected it to spend the year with the Canadian national team , and captained Canada ' s entry at the 1980 Winter Olympics in Lake Placid . Following the 1980 Olympics , Gregg took the unusual step of signing in Japan as a player - coach , and spent two full seasons playing there . 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 4 games . In 1982 – 83 , Gregg emerged as a regular on the Oilers ' blueline , appearing in all 80 games and registering 6 goals and 28 points . 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 . In 1983 – 84 , he would have his finest NHL season , as he recorded career highs of 12 goals and 40 points , and then contributed 10 points in 19 playoff games to help Edmonton win their first Stanley Cup . Following the season , he was selected to represent Canada at the 1984 Canada Cup tournament . Gregg would continue to be a solid contributor over the next few seasons for the Oilers as they dominated the NHL and won the 1985 Stanley Cup , although he would be slowed somewhat by injuries . However , hockey was still something of a temporary career for Gregg , and he was conflicted about when he should leave the sport and take up his medical career . He retired after the Oilers ' disappointing loss in the 1986 playoffs , but changed his mind six weeks into the season and helped Edmonton win their third championship in 1986 – 87 . 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 yet another Stanley Cup . Now in his mid - thirties , Gregg spent two more years with the Oilers as a solid depth defender , helping the team win their 5th 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 . Gregg appeared in 474 NHL games , recording 41 goals and 152 assists for 193 points along with 333 penalty minutes . He also appeared in 137 playoff games , totalling 13 goals and 40 assists for 53 points . Following his retirement , Gregg completed his residency training program at the University of Alberta . He is presently a family physician , operating a successful sports medicine practice in Edmonton .