Clarence 'Hap' Day was the captain for the team's first ten seasons and in 1932, led the Leafs to their first Stanley Cup. He is the only Leaf to have been the Captain, Coach and General Manager of the team. He was inducted into the Hockey Hall of Fame in 1961. Over his 11 years as a Leaf player he played in 581 games totalling 187 points.

Charlie Conacher - 1937-38

Charlie 'the Big Bomber' Conacher, the Kid Line's right winger, led the league in scoring twice, led the Leafs in goals five times and was named an All-Star for five consecutive seasons. Conacher scored the first Leaf goal in Maple Leaf Gardens and went on to score 225 goals in his career of 459 games. Conacher was inducted into the Hockey Hall of Fame in 1961.

Red Horner - 1938-40

Red Horner, a tough and respected defenceman, played with the Leafs for 12 seasons, played in 490 games and led the league in penalty minutes for eight consecutive years. His legendary toughness and ability to defend against the best the league had to offer made him a key member of the Leaf team in the 1930's. Red was inducted into the Hockey Hall of Fame in 1965.

Syl Apps - 1940-43 1945-48

Syl Apps won the Calder and Lady Byng Trophies, was named an All-Star five times and won three Stanley Cups. In his last regular season game, he scored a hat-trick to give him 201 career goals in 423 career games played. His speed and puck handling abilities allowed him to lead on the ice, the respect his teamates had of Syl allowed him to lead in the dressing room. Apps was inducted into the Hockey Hall of Fame in 1961.