Edmonton Oilers

The Oilers have won five Stanley Cups, all during their dynasty years: 1984, 1985, 1987, 1988, and 1990. The first four were won with Wayne Gretzky on the roster, and the 1990 Cup was won after Gretzky had been traded to the Los Angeles Kings. The franchise won its first Cup just five years after joining the NHL from the WHA in 1979.

The Oilers joined the NHL in 1979 as part of the NHL-WHA merger, along with the Winnipeg Jets, Quebec Nordiques, and Hartford Whalers. Prior to that, they had competed in the World Hockey Association since 1972, originally as the Alberta Oilers. The franchise was founded by Bill Hunter.

Wayne Gretzky was traded to the Los Angeles Kings on August 9, 1988, in a blockbuster deal involving players, draft picks, and cash, orchestrated by Oilers owner Peter Pocklington for financial reasons. The trade shocked the hockey world and was seen as a major blow to Canadian hockey fans. Gretzky had already led the Oilers to four Stanley Cups at that point.

Beyond Gretzky, the Oilers dynasty featured Hall of Famers including Mark Messier, Jari Kurri, Paul Coffey, and goaltender Grant Fuhr. Messier captained the team to its fifth Stanley Cup in 1990 after Gretzky's departure. The roster also included key role players like Glenn Anderson and Kevin Lowe.