Nicknamed "The Chief" because of his Native American heritage, George Armstrong played his entire NHL career (1949-71) with the Leafs. He played on four Stanley Cup champion teams and scored 26 Stanley Cup playoff goals during his NHL career. Armstrong was inducted into the Hockey Hall of Fame in 1975.

In 1934, Charlie Conacher not only lead the NHL in goals (36) and points (57), but had a franchise-record 13 game-winning goals as he led Toronto to the Stanley Cup Finals.

During the 1979-80 season, general manager Punch Imlach waged war against his own players, trashing them in the media and banning them from making TV appearances to show that he was in charge. Team captain Darryl Sittler, one of Imlach's favorite targets, was defiant. Because Sittler was protected by a no-trade clause, Imlach instead traded valued line mate and Sittler's best friend Lanny McDonald. When he heard the news, Sittler grabbed the trainer's scissors and cut the "C" off his jersey in protest. After more of Sittler's friends and allies were traded, he resigned as captain and demanded a trade. As a result, one of the greatest Maple Leafs in history became a Philadelphia Flyer.

In 1953-54, Harry Lumley won the Vezina Trophy, presented annually to the NHL's best goalie, with a GAA of 1.86. His 13 shutouts that year was a modern National Hockey League record that stood until Chicago's Tony Esposito recorded 15 in 1969-70.

The Conn Smythe Trophy, awarded annually to the most valuable player during the Stanley Cup playoffs, is named after Conn Smythe, the longtime owner, general manager, and head coach of the Toronto Maple Leafs.

Matts Sundin and the Leafs made history on September 30, 1997, when he replaced Doug Gilmour as captain. Sundin is also the first Swedish player to score 500 goals. He was elected to the Hockey Hall of Fame on 26 June 2012, in his first year of eligibility.

After leading the Maple Leafs in points (45) and assists (29) during his rookie season (1936-37), Syl Apps became the first Toronto player to win the Calder Memorial Trophy. He would go on to play his entire career with the Maple Leafs and win four Stanley Cup championships.

In 1980-81, enforcer Dan Maloney had 20 goals on 80 shots for a career-high shooting percentage of 25%, nearly 10 percentage points higher than his next best year (15.7% in 1979-80).

Future Hall of Famer Reg Noble recorded five hat tricks in Toronto's very first season. He finished the 1917-18 with a team-leading 29 goals and 39 points.

In 1997-98, Tie Domi set a Leafs single-season record with 365 penalty minutes, passing a mark of 351 penalty minutes set by Tiger Williams in 1977-78.