The Edmonton Oilers entered the NHL for the 1979-80 season as one of four World Hockey Association teams that joined the League. The Oilers immediately made the playoffs with a late-season winning streak, finishing with 69 points behind a skinny kid by the name of Wayne Gretzky. No. 99 was ineligible for the Calder Trophy, given to the NHL’s Rookie of the Year (WhA players were deemed to be pros and couldn't win the award) and missed out on the Art Ross Trophy because he had two fewer goals than Marcel Dionne despite tying him for the League lead in points (137). Gretzky did come away with one piece of hardware, however: the Hart Trophy as the NHL’s Most Valuable Player.
In the Oilers' second season in the League, Gretzky set NHL records for assists (109) and points (164), and Mark Messier finished strong with 35 points in the final 24 games of the season. After a three-game sweep of the Montreal Canadiens in the first round of the playoffs, they went on to lose to the defending and eventual repeat Stanley Cup Champions, the New York Islanders.
Three years later, the Oilers began what is now known as the “Dynasty Years” from 1983 to 1990. In ’83-84, the Oilers ran through the regular season behind Gretzky and Messier. Gretzky scored at least one point in the team’s first 51 games. That year the Oilers became the first team in NHL history to have three 50-goal scorers. Gretzky finished with 87, Jari Kurri added 54 and Glenn Anderson finished with 52. The Oilers faced the Islanders in the Stanley Cup Final, a rematch of the previous spring. This time, Edmonton beat the Isles in five games, winning the Cup on home ice and becoming the first team from Western Canada to win the Cup since 1926.
Edmonton repeated as Stanley Cup champions in 1985, overpowering Philadelphia in five games. Kurri tied Reggie Leach's record for goals in one playoff year with 19. The Oilers were unable to pull off the three-peat in 1986, as they lost to the Calgary Flames in seven games in the division finals.
In 1987, the Oilers reasserted themselves as the best team in the NHL, capturing their third Cup in four years by beating the Flyers in seven games. The next season, they beat the Boston Bruins for their fourth Cup in five years, 4-0. In a poll conducted in 2006, the 1988 Edmonton Oilers were listed as one of the top five professional sports teams of the past 120 years.
The 1988 offseason did not play out well for Oilers fans. Team owner Peter Pocklington traded away Wayne Gretzky, Marty McSorley and Mike Krushelnyski to the Los Angeles Kings for $15 million U.S., Jimmy Carson, Martin Gelinas and the Kings’ first round picks in 1989, 1991, and 1993.
Despite losing Gretzky, the Oilers went on to win the team’s fifth Cup in seven years in 1990. Mark Messier, Glenn Anderson, Jari Kurri, Kevin Lowe, Randy Gregg, Charlie Huddy and Grant Fuhr were all a part of each Cup victory. The Oilers haven't won since then, though they did make a surprise appearance in the Final in 2006, losing to Carolina in seven games. They are trying to end a four-year playoff drought with a core of young talent that includes No. 1 draft pick Taylor Hall.