[6][7][8] The rivalry gets the "401" nickname from Ontario Highway 401, which forms most of the standard driving route between the two cities (with the remainder being Quebec Autoroute 20),[9] as well as the Two Solitudes book and cultural phenomenon.

Their main rivals were the Rochester Rhinos and the Toronto Lynx prior to the latter's move to the USL Premier Development League.

The modern day rivalry involving Toronto FC came into fruition during the first ever Canadian Championship, Canada's domestic cup competition that was formed in 2008.

Played on May 27, 2008, Toronto emerged victorious 1–0 over thanks to a Marco Vélez goal in the 72nd minute in front of a crowd of 12,303 at Saputo Stadium.

Ultimately, though, the Impact ended up winning the three-way tournament, against Toronto and Vancouver Whitecaps, achieving the first Canadian Championship after posting a 2–1–1 record.

Toronto got revenge on the Montreal at the following Canadian Championship by scoring six unanswered goals in a come-from-behind 6–1 win at Saputo Stadium.

The match also secured Toronto's place in the 2009–10 CONCACAF Champions League, where they were eliminated in the preliminary round of the tournament.

The Reds continued their reign of dominance in the 2010 edition of the Canadian Championship, beating Montreal in both the home and away legs of the competition, tallying an aggregate score of 3–0 during that time.

Bosnian Siniša Ubiparipović netted the opening goal of the derby in MLS competitions, scoring for Montreal in the 18th minute.

Andrew Wenger, the first pick of the 2012 MLS SuperDraft, netted in the 81st minute to give the Impact the game-winning goal.

During their 2013 Canadian Championship run, the Impact defeated Toronto by a 6–0 scoreline, to date, the largest margin of victory in the derby history.

[15] On April 24, 2013, Justin Braun became the first player to play for both sides of the derby, after he was traded from Montreal to Toronto over the winter break.

Collen Warner repeated the feat in 2014 after being traded to Toronto for Issey Nakajima-Farran, who had never played against Montreal before the exchange.

Dominic Oduro (2015) and Kyle Bekker (2016) later joined the turncoat club, both playing for Toronto before Montreal.

Additionally, the club is supported by several other supporter's groups including Original 109 who sit in Section 109 of BMO Field, SG114 who sit in Section 114, and the Tribal Rhythm Nation who represent the African, Caribbean and Latin American communities in the Greater Toronto Area.

For marquee matchups, such as games against acclaimed opponents, rivals, or Champions League fixtures, as well as winter-time matches, both teams sometimes play in larger, indoor stadiums in their respective region.