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Top 5 Canadian Classiques between Toronto FC and CF Montréal

We take a look at some of the biggest matchups between Toronto FC and CF Montréal in history and rank them from 1-5.

SOCCER: NOV 30 MLS Conference Final Leg 2 - Impact at Toronto FC
Toronto FC’s Jozy Altidore in action against CF Montréal’s Victor Cabrera during the 2016 Eastern Conference Finals
Photo by Kevin Sousa/Icon Sportswire via Getty Images

Maple Leafs vs Canadiens. English vs French. Hawaiian Pizza vs Poutine. Drake vs Celine Dion. Waking The Red vs Mount Royal Soccer.

The Toronto-Montréal rivalry runs deep in the history of our beloved nation, with another chapter being written in the tale of the cities this Sunday, as Toronto FC take on CF Montréal in the Canadian Championship final in what is a season-defining game.

A showdown that has truly revolutionized Canadian soccer, the 401 Derby has provided for some classique moments over the years, so let’s take a trip down memory lane and take a look at the five most historic matchups between the two Canadian rivals.

#5. Fall from Playoffs Grace

CF Montréal 3-0 Toronto FC, 2015 MLS Cup Playoffs Knockout Round

In terms of all-time classics for the neutral fan, this game would not come near the top five. But the history-breaking magnitude of this matchup helps it sneak on this list, arguably a pivotal part in the rise of the sport in Canada. The first time ever that two Canadians teams met each other in the MLS Cup Playoffs, looking to cement their place in the Canadian soccer throne by becoming the first Canadian team to win a playoff game.

For the Reds, this was the pinnacle. Known as a laughing stock across the league since its arrival in 2007, after being dubbed as “the worst team in the world” by their own star striker, TFC had finally made it to the promised land with a chance to show that they deserved to be there. CFM had fallen in knockout round the previous year to the Houston Dynamo and were looking to make it past one more hurdle this time around.

With the final day of the regular season just four days before the knockout round, we were fortunate enough to see a preview between Toronto and Montréal with Didier Drogba terrorizing yet another team wearing red as he did throughout his time in England. With that final day win, Montréal assured they would play Toronto in the knockout round, in their own backyard for the first time ever in the playoffs.

A game of many firsts ended with another first for TFC, a first playoff loss, losing 3-0 due to a 20 minute-long lapse of concentration in the first half, seeing Drogba net another against the Reds. This disappointing result would be the beginning of a gradual climb through the playoffs over the coming years for Toronto, facing off against their nemesis once again later down the line.

#4. 94:25

Toronto FC 2-1 CF Montréal, 2017 Canadian Championship Final - Leg 2

2017 Canadian Championship - Toronto FC v Montreal Impact - Leg 2 Photo by Adam Pulicicchio/Getty Images

Did I just steal Manchester City’s iconic 93:20 slogan? Did I compare Sergio Agüero’s title-winning goal against Queens Park Rangers to Seba’s versus Montréal? Absolutely, because the ground-shaking elation from the Toronto faithful once that ball passed the helpless Maxime Crépeau with seconds remaining, that was European-esque.

After a 1-1 draw in the first leg at Stade Saputo, the Reds were having flashbacks to the year prior after falling down 1-0 in the second leg. A goal from the Atomic Ant early in the second half set up for a cagey affair, but a red card for Montréal’s captain Patrice Bernier invited late pressure from TFC.

What seemed to be bound for an extra 30 minutes was cut short, as a strong challenge from Giovinco prevented a Montréal counterattack, before finishing off the play himself and celebrating into the thunderous crowd.

Not only was this goal an iconic moment in the history of this rivalry, but it was the start of the road for Toronto in what would become the best season in their existence. I mean, what better way to begin a treble than against your rivals.

#3. The Montréal “Paintjob”

CF Montréal 3-2 Toronto FC, 2016 Eastern Conference Finals - Leg 1

Toronto FC plays the Montreal Impact in the MLS Conference Finals in the MLS Cup Playoffs Steve Russell/Toronto Star via Getty Images

Firstly, Bret did not screw Bret. But Montréal’s grounds crew definitely screwed Montréal’s grounds crew.

In what easily could have been overshadowed by the pre-game catastrophe turned out to be a masterpiece of the sport. It had all that anyone could want from a soccer game. There was the joy and celebrations for the home team, the villainous comeback story, the controversial goal, all in front of the jam-packed Olympic Stadium full of 61,004 strong voices, the most that the Canadian Classique has ever welcomed.

A year after playing each other in the knockout round, both teams made progression and met in the Eastern Conference Finals, with the stakes as high as they possibly could be: the chance to be the first Canadian team to play in the MLS Cup final.

After taking a 3-0 lead early in the second half, Montréal fans were already planning their flight for the final date, as Toronto fans must have thought they were having a déjà vu moment from their exit in 2015. However, two goals from Michael Bradley and Jozy Altidore got TFC back in the tie, overcoming the hostile Montréal crowd and their green lasers.

With the tie still up in the air, this match helped move eyes in the direction of Canadian soccer, with many tuning in to see the outcome of the second leg, even after the earlier embarrassing painted lines malfunction. But at least there was one absolute gem that we got out of that calamity.

#2. Miracle in Montréal

CF Montréal 1-6 Toronto FC, 2009 Canadian Championship

A game that is so deeply carved into the folklore of these two teams, that it even has its own name. One of the earliest encounters between these two sides, but to this day still remains as one the most defining moments for the journey to come.

The second edition of the Canadian Championship had come down to the final fixture, with Toronto needing to enter Montréal and decimate them by at least four goals to climb into first place over the Vancouver Whitecaps. Back then, TFC were the only Canadian side in MLS and were easily favoured to devour through the Canadian competition, but after losing the inaugural Canadian Championship to the neighbours from the east in a shocking turn of events, this was a chance to make up for the embarrassment the year prior for the Reds.

An unforgettable night for Toronto, but a gloomy night for those home fans as they watched Srdjan Djekanović pick the ball out of his net six times, three times courtesy of the Scarborough Walk of Fame star himself, Mr. Order of Ontario, Dwayne De Rosario.

May 28, 2009 Toronto FC player Dwayne De Rosario Scarborough at the 4th annual Scarborough Walk of F Photo by Andrew Francis Wallace/Toronto Star via Getty Images

They needed to overcome an impossible task and win by four goals, but they conquered and walked out of Québec with a five-goal difference, just to rub salt in the wounds. This sign of dominance was just the first of much more to come, with the boys from Ontario successfully defending their title as Canadian Championship winners for the next three years in a row.

#1. Kings of the North

Toronto FC 5-2 CF Montréal, 2016 Eastern Conference Finals - Leg 2

Toronto FC beat the Montreal Impact 5-2 in the second game to win the Eastern Conference Finals and to advance in the MLS Cup Final Steve Russell/Toronto Star via Getty Images

Best playoff series ever. If the first leg had everything that the soccer fan would want to see, the second leg had everything to make the non-soccer fan to fall in love with the beautiful game.

Coming off of an eventful showing in Montréal, both teams delivered a game for the ages on this cold night in Toronto full of moments of jubilation and stress for both fanbases. Toronto yet again fell behind early, but you just knew from that moment, it was a special night to come. Even with former TFC player Dominic Oduro shushing the home crowd, the atmosphere got louder after going down 0-1, and the electricity at BMO Field did not die one bit.

After sparking a first half comeback through goals from Armando Cooper and Altidore, the Reds went into the break in position to advance to the MLS Cup Final, but a quick response from Ignacio Piatti meant TFC needed a goal to avoid elimination. Right when we needed him the most, out of nowhere comes a flying Nick Hagglund to even the tie on aggregate, which would go the distance into an extra 30.

With Seba going off injured, I’m sure there were many Toronto fans panicked about advancing without their star designated player and most reliable penalty kick taker, but it was the man who came onto the pitch to replace the Italian that would score the winning goal.

It should be dubbed “The Benoît Cheyrou Game”. That diving header was the perfect way to end the tie, but TFC again wanted stronger assurance of their ticket in the final, with Canadian Tosaint Ricketts adding a 5th. With the 5-2 win, it was the boys in red who ended the night dancing in the rain.

There are plenty more iconic moments to come from matchups between Toronto and Montréal, hopefully one is awaiting us tomorrow, to end this 2021 season on a final high.