The 1928–29 Toronto Maple Leafs season featured the first playoffs appearance.
After finishing in third position in the Canadian Division, the Maple Leafs defeated the Detroit Cougars before losing to the New York Rangers in the semi-finals.
Teams that qualified for the playoffs are highlighted in bold.
In their first play-off appearance the Maple Leafs met the Detroit Cougars in the two game total goals quarter-finals, and won 7–2.
The Leafs next faced the New York Rangers in a best-of-three series, losing 2–0.