TORONTO – The path to lifting the Voyageurs Cup has a history of late drama and pivotal moments.

All three series-opening legs of the Canadian Championship second qualifying round this week – each an all-Canadian Premier League affair – saw just such potentially crucial passages.

In Tuesday’s 1-1 draw between Forge FC and Cavalry FC in Hamilton, it was the late penalty kick that saw the visitors grab a valuable equalizer and precious away goal from the penalty spot when Quillan Roberts brought down Dominique Malonga in the box.

Come Wednesday on the East Coast, it was a 140-second spell that saw HFX Wanderers FC respond to Valour FC’s early dominance and opening goal with a ball that may, or may not, have entirely crossed the line off the head of Tomasz Skublak and Mohamed Kourouma scoring moments later to give the hosts a 2-1 lead as they head into next week’s second leg.

And after three York9 FC headers seemed to all but seal their spot in the next round, Oumar Diouck breathed life into visiting FC Edmonton with an away goal, only for another bit of stoppage-time drama to pounce as a potential second Eddies strike was ruled out for a supposed foul, forcing them to return home with a 3-1 deficit in tow.

In the course of a long season, whether 10 games or 40, there are plenty of such moments, but their importance is obscured. Rarely does a single one prove decisive in the way that they can in cup play.

Of course, there are crucial moments, clinching goals, and such, but where the season is a marathon, an accumulation of all instances over its span, the cup often comes down to singular moments or at least very few of them.

That is what makes the cup special.

A two-legged series of 180 minutes, and on occasion extra time and penalty kicks, can come down to individual moments. That is the magic of the cup.

York9 coach Jimmy Brennan knows a thing or two about cup magic, having cut his teeth on the grand-daddy of all cup competitions, the FA Cup during his decade in England.

“It’s the midweek game under the lights, a little bit of rain, something on the line, knowing that there is a home and away game, and that carrot that’s dangled in front of you of what is in the next round,” summed up Brennan on Wednesday night after York9’s first leg victory. “These are great, cup matches.

“Even playing against (AS) Blainville, it’s great playing the lower league teams. Now we’re playing against our own teams, and, hopefully, we get another great game in the next round if we can get through this.”

That the reward, progression to the next round or the trophy itself, is so immediate heightens every second of the game. That moment, the one that will be talked about for years, can come at any time.

For its first six seasons, the Voyageurs Cup, created and furnished by supporters, was awarded via in-league play, with the Montreal Impact, then playing in the USL A-League/First Division, winning each time.

Since the advent of the tournament proper in 2008, despite humble origins and limited stature, the Canadian Championship has a long history of providing the drama and controversy one expects of a cup competition.

In the first edition, there was Roberto Brown’s equalizer for the Montreal Impact at BMO Field against Toronto FC in 2008. The round-robin format punished the sole MLS side in the competition, as they did not lose to champions Montreal, but took only one point from Vancouver, who lost both matches to the Impact, allowing the Quebec-side to continue their dominance to that point.

From the off, the competition proved fair was a relative term.

That year marked the first and only time that a ‘lower league’ side has lifted the trophy. Brennan was on the pitch that night, captaining a Toronto side that was forced to watch the Impact celebrate on their turf.

The following year witnessed the Miracle in Montreal, where Brennan and TFC had their calculators out, repaying the Impact and taking advantage of the format themselves, as the goals piled in – with Vancouver Whitecaps FC, who were in line to hoist the cup had Montreal put up a fight, in attendance, watching in horror as Toronto won 6-1.

In 2011, where the format changed to the current two-legged affairs with the addition of Edmonton, the second leg of the final between Toronto and Vancouver was abandoned after an hour with the field deemed to be in unplayable conditions following a torrential downpour, despite Eric Hassli having put the Whitecaps in the driver’s seat with an away goal that put Vancouver ahead and cancelled out TFC’s from the first leg.

Teitur Thordarson’s protestations went unheard and that leg would controversially be restarted from scratch a week later, Hassli’s goal annulled. Camilo would score early for Vancouver, resetting the reset, but a Joao Plate penalty kick and a Mikael Yourassowsky strike in the second half rained on Vancouver’s hopes of lifting the cup for the first time.

In 2013, Edmonton were minutes away from putting themselves in good stead for a giant-killing by handing Vancouver a first-leg defeat (with York9’s Michael Cox scoring for the Eddies), only for goals in the final ten minutes from Camilo and Tommy Heinemann to turn the tide at Commonwealth Stadium, dooming their hopes of progressing.

The next season, 2014, Edmonton would again nearly take that step, defeating Montreal 2-0 in the first leg, and pushing them to the limit in the second, only for 97th minute Patrice Bernier penalty kick for a supposed handball to overturn the series, handing the Impact a 5-4 aggregate victory – Jeff Paulus certainly hasn’t forgotten that one.

The Eddies would feel robbed again in 2015 having taken a 1-1 draw from their visit to Vancouver in the first leg of their semifinal series. A Pedro Morales penalty kick would swing the series in the Whitecaps way come the second leg in Edmonton, only for Tomi Ameobi to seem to send the match to extra time from the spot in the 91st minute.

But Matias Laba had other plans, scoring in the 97th minute to seal Vancouver’s spot in the final – the Whitecaps would finally lift the cup that year, ending their long wait.

2016 would be no different. A highly-debatable red card to Impact legend Bernier in the semifinals against TFC was a major talking point, seeing the Reds into the final, where the Whitecaps looked set to repeat, only for Will Johnson to sacrifice himself for the 95th-minute strike that handed TFC the trophy on away goals.

And Sebastian Giovinco would provide the late-decider the next year, in the 95th minute at BMO Field, much to the Impact’s chagrin.

Just last year, with Vancouver looking to take a 2-1 lead on the road, a 96th-minute own-goal from former Toronto homegrown defender Doneil Henry would shift the balance, gifting Toronto a draw and a second away goal. TFC would end up winning a third-straight cup handily back home.

Whenever the Voyageurs Cup is on the line, late drama ensues, that much is certain. The probability that there will be controversy is high, but just where and when it will strike is never certain.

With reminders in all three first legs this week, dare any rule out that the return matches next week could provide even more such fodder for the annals of cup lore?

And with this year’s expanded edition, there will be ever more opportunities.

“These are special moments,” concluded Brennan with York defender Luca Gasparotto nodding in agreement. “It’s great to see that this cup is growing with more teams coming in.

“It’s exciting times. When you look anywhere around the world, the league cup games are special ones. You can see the Voyageurs Cup is just going to get bigger and bigger every year and a lot more prestigious than it already is.”

Not that everyone will be pleased with the outcomes.