Edmonton Oilers

After joining the NHL, the Oilers won the Stanley Cup on five occasions: 1983–84, 1984–85, 1986–87, 1987–88, and 1989–90. Along with the Pittsburgh Penguins, they are tied for the most championships won by any team since the NHL–WHA merger, as well as the most won by any team that joined the league in or after 1967. Among all NHL teams, only the Montreal Canadiens have won the Stanley Cup more times since the league's 1967 expansion. The Oilers also won six straight division titles from 1981–82 through 1986–87. However, the Oilers have not won a division title since 1987, a drought that includes their most recent two Stanley Cup wins. It is the longest division title drought in all of the North American major professional sports. For their overall success in the 1980s and early 1990s, the Oilers team of this era has been honoured with dynasty status by the Hockey Hall of Fame.

The Oilers struggled after coming up short in the 2006 Stanley Cup Final, missing the playoffs for the subsequent 10 seasons. The team made 16 first-round selections in the NHL entry draft from 2007 to 2019: 11 within the first 10 picks overall, six within the first four picks, and four of the first overall selections. With those first overall picks, Edmonton selected Taylor Hall, Ryan Nugent-Hopkins, Nail Yakupov, and Connor McDavid; of these, Nugent-Hopkins and McDavid remained with the team, helping them reach the Stanley Cup Final in 2024 and 2025, where they lost to the Florida Panthers on both occasions.