CF Montréal and Toronto FC have met in two of the last three Canadian Championship finals, taking home a Voyageurs Cup trophy and Concacaf Champions League berth apiece across 2019-21.

They're a subsection of rivalry-laden moments these Canadian Classique foes have shared in recent years, and now another chapter awaits Wednesday evening when Toronto host Montréal at BMO Field in a Canadian Championship semifinal (7 pm ET | OneSoccer).

Toronto captain Michael Bradley knows exactly what’s at stake, with the winner advancing to face either Vancouver Whitecaps FC or Canadian Premier League side York United in the all-decisive final in July.

“It’s Toronto-Montréal, it’s everything that goes with that,” said the former US men’s national team midfielder. “It’s the history of the two cities, it’s the history of the two clubs. It’s the cultural differences between the two cities, it’s the pride of the two cities. Everything plays into it, right? As with any rivalry, that only builds over time. It doesn’t go away.”

This will be 2022's first Canadian Classique edition, setting the stage for MLS regular-season matchups on July 16 and Sept. 4. And it comes with the clubs heading in different directions, as Toronto struggle amid a period of near-wholesale transition under head coach and sporting director Bob Bradley, anticipating the imminent summertime arrival of Italy star Lorenzo Insigne and possibly other key additions.

As for Montréal, they’re on an upward trajectory under manager Wilfried Nancy and have been led by midfielder Djordje Mihailovic, an early Landon Donovan MLS MVP frontrunner who’s chasing a USMNT breakthrough ahead of the Qatar 2022 World Cup this November.

That leaves the clubs at opposite points in the Eastern Conference standings, with Montréal in fifth place and Toronto in 12th place. But that doesn’t detract from the emotions that await.

“Over the years, you know that the pressure in the semifinals is always really big because obviously it’s all about getting to a final,” Bob Bradley said. “That’s what’s so special for a club, for players, for fans. This game takes on that extra level of everything because it’s not only Montréal but it’s this idea that, ‘Come on we’ve got to get in another final, we have to have a chance to play for another cup.’”

Toronto won the retroactive 2020 Canadian Championship final roughly three weeks ago, beating CPL side Forge FC in penalty kicks in a match that was delayed nearly two years because of the COVID-19 pandemic. That injected some momentum and positivity into the side, giving Toronto’s youth-filled group a taste of high-magnitude games.

Montréal have played in big matches themselves already this year, reaching the CCL quarterfinals. They beat Liga MX’s Santos Laguna in the Round of 16 before falling to Cruz Azul in the next stage.

Montréal defender Alistair Johnston, an offseason trade acquisition from Nashville SC, wants another test in pressure-packed moments.

“For teams like us in MLS – us, the Whitecaps and Toronto – if you’re not lifting that Canadian Championship at the end of the year, it doesn’t matter what you do in the league, it can always kind of be seen as a blemish,” said the Canadian international. “So we know there’s a lot of pressure on the line in terms of that. This is the best way to go and win a trophy, the easiest way to a degree. We know this is a really big opportunity to kick on in the second half of the season and it starts with performances like this.”

Consider the stage set, bringing together historic rivals in a cup competition before the dog days of MLS truly get underway.

“When you go into a rivalry match, I think you can throw form out the window a little bit,” Johnston said. “Both teams are going to be up for it.”