High Quality Content by WIKIPEDIA articles! The 1988–89 Calgary Flames season was the 9th season for the Calgary Flames and 16th for the Flames franchise in the National Hockey League (NHL). They won their second consecutive Presidents` Trophy as the NHL`s top regular season club and went on to win the first Stanley Cup championship in franchise history, defeating the Montreal Canadiens in the 1989 Stanley Cup Final. Al MacInnis won the Conn Smythe Trophy as the most valuable player of the playoffs.