The rivalry is largely bolstered because of the proximity between the two teams, with Toronto and Detroit approximately 370 kilometres (230 mi) apart, connected by Ontario Highway 401, and a number of shared fans in between the two cities (particularly in markets such as London, Sarnia, and Windsor).

The club scored in double digits for the first time in its history against the Maple Leafs, in a 10–1 rout at Olympia Stadium on December 25, 1930.

[2] The 1940 Stanley Cup semifinals between the Maple Leafs and Red Wings was especially notable with the second game evolving into a brawl.

The tone of the game was set early when Maple Leafs' defenceman, Rudolph Kampman, injured Red Wings' forward Cecil Dillon who became unable to play the rest of the night.

[3] Later in the same frame, Red Wings' Don Grosso lifted Maple Leafs' Hank Goldup over the boards, dropping him on the cement floor.

The game ended in a near-riot when in the final minute, Red Wings' Eddie Wares drew a misconduct penalty and then a $50 fine for arguing and refusing to leave the ice.

Referee Mel Harwood dropped the puck for the faceoff while Wares was still on the ice and he promptly called a too-many-men penalty on Don Grosso.

At the end of the game, Red Wings' coach Jack Adams attacked Harwood, punching him in the face following a profanity-laced outburst.

"[8] Rookie Gaye Stewart, who joined the club for the fifth game of the final, became the youngest player to win the Stanley Cup at the age of 18 years, and nine months.

The rivalry heightened to a fever pitch due to an incident in the 1950 playoffs when the Red Wings' young star, Gordie Howe, mistimed a check on Maple Leafs' Ted Kennedy and fell head-first into the boards, suffering severe injuries and needing emergency surgery to save his life.

[2] The rivalry grew so fierce that when the New York Rangers reached the 1950 Stanley Cup Finals to face the Red Wings, but could not play in their home rink, Madison Square Garden, because the Ringling Bros. and Barnum & Bailey Circus were using the arena, New York arranged to play home games in Toronto, whose fans held a deep enmity against the Red Wings.

Angered over a magazine article where Kelly had suggested the Red Wings forced him to play with a broken ankle in the 1958–59 NHL season, Adams traded the all-star to the Maple Leafs.

When the Maple Leafs eliminated the Red Wings in the 1960 playoffs, Kelly couldn't resist another jab at Adams, telling the Ottawa Journal "it's nice to be with a winner.

[13] On March 27, 1973, Mickey Redmond scored two goals on Maple Leafs goalie Ron Low in a span of 18 seconds to become the Red Wings' first ever 50-goal scorer in an 8–1 victory.

Maloney was charged with assault causing bodily harm, part of a crackdown on hockey violence by Ontario attorney general Roy McMurtry.

A plea bargain left Maloney performing community service work while being banned from playing in Toronto for two years.

[13] On January 13, 1986, the Maple Leafs and Red Wings played a regular season game that involved a brawl lasting nearly 20 minutes.

[14] During the brawl Maple Leafs assistant coach John Brophy attempted to engage Park, although he was held back by the usher.

In the seventh game of the 1993 Norris Division semifinals, Maple Leafs' Nikolai Borschevsky's shot the game-winner in overtime past Red Wings goaltender Tim Cheveldae hushing the fans inside Joe Louis Arena.

The goal gave the underdog Leafs a shocking first-round series victory over Steve Yzerman's heavily favoured Red Wings.

Borschevsky's game seven overtime goal gave Toronto the series and made them the sixth club to eliminate a team with a better regular season record in the first round of the playoffs.

[15] Playing in the same division for the first time since 1998, the Red Wings hosted the Maple Leafs for the 2014 NHL Winter Classic at Michigan Stadium in Ann Arbor.