 The following season , the Oilers and Islanders met again in the playoffs . The Oilers won the rematch in five games , marking the start of another dynasty . Led by Wayne Gretzky and Mark Messier , the Oilers won five Stanley Cup championships between 1984 and 1990 . The Oilers won two consecutive Cups in the 1983 – 84 and 1984 – 85 seasons , and in the 1986 – 87 and 1987 – 88 seasons . They also won a Cup in the 1989 – 90 season . The Oilers ' Cup streaks were interrupted in the 1985 – 86 and 1988 – 89 seasons by two other Canadian teams . Edmonton 's hopes for a third consecutive title in 1986 were dashed by their provincial rival , the Calgary Flames , after Oilers ' rookie Steve Smith accidentally bounced the series @-@ winning goal off goaltender Grant Fuhr and into his own net . Smith 's error remains one of the most legendary blunders in hockey history . The Flames were defeated by the Canadiens in the finals , as rookie goaltender Patrick Roy led Montreal to their 23rd Stanley Cup . The 1989 final was a rematch between the Flames and the Canadiens and was won by Calgary , which captured its only championship in franchise history . The Flames also became the only team to defeat the Montreal Canadiens for the Stanley Cup at the Montreal Forum . 
