There’s a reason it’s called the magic of the cup.

Toronto FC will begin the quest to lift their ninth Voyageurs Cup on Wednesday night when Simcoe County Rovers FC come to BMO Field.

The Canadian Championship is a highlight of the soccer calendar – in the cup, anything can happen.

And over the years, it has.

Since those earliest days when the competition was fought between just the three MLS clubs it has grown immensely. This year’s edition, the seventeenth, will feature 14 teams, drawing in clubs from the Canadian Premier League and the divisional champions from League1 Canada. It will only get bigger from here.

The visit of Barrie, Ontario-based Simcoe County on Wednesday marks the first time TFC have faced off against a representative of League 1 Ontario.

On paper the gap between the two clubs is wide, but John Herdman knows that in the cup all that goes out the window.

“Watching cup games, what you always know is that there's a few banana skins in those opening rounds. There's always some upsets and surprises. If I'm sitting in the Simcoe camp, they'll be pretty excited and hoping for the one of the biggest upsets in Canadian football history,” imagined the TFC coach on Tuesday afternoon. “You either look at that as a curse or as an opportunity and it's probably a little bit of both.”

“Coming into a match like this, for us, it's about advancing to the next round,” Herdman underlined. “Winning the cup is on the agenda for this group of players and we'll be coming into this with full commitment to get the job done.”

Toronto have not lost to a non-MLS side in the competition in some time: a 2-1 defeat in the opening leg of a semifinal tie against Ottawa Fury FC in 2017. TFC would advance 6-1 on aggregate following the second leg at home.

CPL challengers York United and Pacific FC have both come and fallen at BMO Field, as did HFX Wanderers FC when Toronto travelled to Halifax. Forge FC pushed the Reds to penalty kicks in the much delayed 2020 Final (played in June 2022), but even at home in Hamilton they too could not unseat Toronto.

It’s Simcoe County’s turn to have a go.

With league fixtures on either side of the midweek clash, Herdman will manage his squad accordingly. He always had this match pencilled in as a spot for players outside the core group to get a chance. Injuries have altered the planning to this point, but that intent remains.

“We knew through this Phase Three, [as] we call it, that there would be limited roster rotation – that's what I said at the beginning and then it was ‘next man up’ from the first week, so I regret saying that, but there have been some players that haven't seen the field,” Herdman explained. “I'm anticipating they'll get a lot of minutes to feel part of the group and to take a step forward in a big competition."

"Rotation wise, obviously I've got Orlando in mind at the weekend, but this game is front and centre," he added.

"And we'll do everything we can to put our best foot forward.”

He’s noted an “excitement” as the match approaches.

“That group are hungry,” Herdman said. “[They] want to earn more minutes out of this game and play in front of our fans.”

Preparing for an opponent that is yet to play a league game this year is never easy – L1O’s Men’s Premier kicks off this weekend.

“We managed to get quite a few games from last year, but they've changed the coach. There was a friendly match against York we were able to scout that a bit,” laid out Herdman. “We've gone through the process of just saying we'll focus on us this week.”

“If we impose ourselves the way that we can at home, there's a certain style that you're expecting then, and you put the opposition into positions where [it] can be more predictable,” he anticipated. “We've worked on the things we think we can control and outside of that, you know set-pieces, transitions, you have to be really dialed in on something that has cost us in recent games.”

With Canadian internationals past and present Doneil Henry, Janine Beckie, Atiba Hutchinson, and Julian de Guzman cheering on Simcoe County as part owners, Herdman was inspired to pull an old file from his Canadian Men’s National Team days.

“I took the template [from] when we played USVI [US Virgin Islands] or Aruba,” he said. “Teams that it’s a David and Goliath story, they have a mindset, they typically have a style of play they want to come in; you know your biggest enemy is your own frustration and the motivation equation of it's not quite gone how you expected it, etc.”

“We did a little bit of work on the mindset this morning,” Herdman continued. “We set some targets for the game, some very clear targets. I always feel like that tends to supersede the motivation element, that it's a massive game for them.”

“We've set a pretty ambitious target for our team as well for this match. It's not just going to be one of those games where guys are picking up minutes and getting the chance to prove themselves,” he added.

“They are going to have to work as a team to hit the goals that we've set internally, it will have to be a real team performance.”

TFC are ready.

“The attitude is good,” said Kobe Franklin. “You have to have the same attitude going into every game. The same mindset that the team wants to perform.”

“The attitude and the culture stays no matter who we play,” he stressed. “So making sure that everyone is sharp in training and treating this just as any other game.”

Playing in the Canadian Championship will be a particular treat for the young local guys who get the chance.

Herdman confirmed that some faces from TFC II would be added to the squad.

“Yeah, there will be a couple of call-ups,” he said. “We'll announce that a little bit later. We're just finalizing all the paperwork. Some young men who have been proving themselves in the preseason and who've been training with us as well.”

Franklin can’t wait.

“I grew up watching it as a Canadian kid,” he said.

“Seeing Toronto FC winning so many titles during our short history has been very good, so I’m looking forward to diving into this year's one and hopefully getting the trophy in the end.”

The coach did have one final note of caution.

“You can't put attention on the scoreboard in these matches. The clock and the scoreboard is your worst enemy,” Herdman reminded. “It's about process.”

“That's where we put the attention today. Typically a match-day minus one is more light, but we got right down to process today and the guys were dialed in,” he closed. “You can see just how motivated they are to play this match. We won't be looking at the scoreboard, we won't be looking at the clock. It's just on task, whistle-to-whistle, and the outcome they've set themselves... we'll look at that at the end of the game.”