The 1965–66 Toronto Maple Leafs season was Toronto's 49th season in the National Hockey League (NHL).
For the fourth straight year, Toronto met Montreal in the first round.
The Canadiens were victorious over the Leafs in four straight games.
[2] The Maple Leafs were involved in the following transactions during the 1965–66 season.
The Maple Leafs opted not to participate in the 1965 NHL Amateur Draft, which was held on April 27, 1965, at the Queen Elizabeth Hotel in Montreal.