May's madness would continue, but the unbeaten run would not, as Toronto FC began the month with a 3-0 loss to the New England Revolution on June 3, only their second defeat of the season.
A well-earned break would lead into another hectic spell of four matches in 10 days, including the two legs of the Voyageurs Cup final against the Montreal Impact.
Toronto would kick start that stretch and return to winning ways on June 17, defeating DC United 2-0 at BMO Field on goals from Jozy Altidore and Jordan Hamilton, the three designated players combining to open the scoring on the hour mark in a goal not unfamiliar to one that lay ahead.
Depth would once again be tested, a recurring theme of the campaign, as Greg Vanney cycled through his roster without skipping a beat.
In the first leg of the Canadian Championship on June 21, TFC and the Impact would draw 1-1 at Stade Saputo with Matteo Mancosu and Jozy Altidore exchanging goals.
TFC would respond to the earlier loss in New England, beating the Revolution in Toronto with a gutsy 2-0 win on June 23, on just a single days' rest. Drew Moor would open the scoring with a striker's finish at the back-post, while Alex Bono came up huge to deny Teal Bunbury late, before Sebastian Giovinco provided a stoppage-time cushion to the victory.
Drought over, Giovinco was heating up just in time to take centre-stage.
As if a Voyageurs Cup match could finish any other way, recall Will Johnson's heroics in the 2016 edition, there was drama and fireworks in the second leg with Toronto handing Montreal a late 2-1 defeat on June 27 to claim a second-straight and sixth overall title, solidifying their berth in the 2018 CONCACAF Champions League.
Ballou Jean-Yves Tabla opened the scoring for the visitors, cancelling Toronto's away goal advantage from the first leg. But Giovinco, in vintage form, would create his own space for a low finish in the second half, teeing up the late action.
The match would be remembered for the ending: a late Patrice Bernier red card, the ensuing shoves, a last-kick winner from Giovinco, teed up by Raheem Edwards, both of whom made their way to the South End, along with their jubilant teammates, to celebrate with the faithful, though one had more difficulty getting over the advertising boards than the other.
Giovinco, who was named the George Gross Memorial Trophy winner for his MVP performance, manned the drum in the post-match celebrations.
But the milestone was not without cost, as Steven Beitashour would be sidelined for weeks with severe injury suffered in a massive collision with Kyle Fisher on the cusp of half-time.
The Voyageurs Cup, the first major trophy of the season, would join the Trillium Cup in TFC's wake. A check-mark along the way, it was then that the club first declared they had a historic treble squarely in their sights.