Never satisfied, Toronto FC entered the final month of the campaign with two matches remaining, as the post-season beckoned.
For the third time in a calendar year, the Montreal Impact, on October 15, would have to watch Toronto hoist a trophy. First came last season's Eastern Conference Championship, then this summer's Voyageurs Cup, the 2017 Supporters' Shield was yet another slight against Canadian cousins.
Shield preparations well-made, Montreal, the most reviled of rivals, would not provide a guard of honour.
The task of adding to the indignity would fall to Jozy Altidore, who scored the only goal in a 1-0 win on that day. Alex Bono proved his worth again, making several key saves in the tightest of matches, while plenty of posts were hit on both sides.
With the win, Toronto achieved two more milestones: their 20th win of the season tied the record for most in the post-Shootout era, while the three points brought their total to 68, equalling the mark set by the 1998 LA Galaxy as most in a season.
As Decision Day loomed, Toronto were intent on breaking that points record and anticipated a playoff-type atmosphere away to Atlanta United on October 22.
A VAR-induced penalty kick would open the scoring, but in-form Altidore pounced on some loose defending to level, Sebastian Giovinco taking a sip in celebration.
Atlanta would retake the lead, but well-fuelled, Giovinco would have his say, striking another scintillating free-kick, his sixth of the season – a new MLS record – to secure a 2-2 draw.
With Altidore's goal, for the first time in club history TFC had two 15-plus goal-scorers, Giovinco having finished with 16 of his own. The point not only pushed Toronto past that long-standing points record, but also ensured that the 12-point shield-winning cushion was the largest in MLS history.
Points record achieved, shield in tow, Toronto now had to overcome the weight of history; some call it a curse, others an opportunity.
Some were braced for a hostile homecoming, carrying the label of favourites is never easy, Toronto began the Audi 2017 MLS Cup Playoffs on the road in the first leg of the Eastern Conference Semifinal on October 30 at the New York Red Bulls.
It was MLS Cup or bust for TFC after last season's disappointment. They knew well what Red Bull would throw their way. The time had come to embrace that challenge.
Greg Vanney had options at his disposal, some he would use over the next several weeks as the five playoff matches would contain many a twist and turn.
Victor Vazquez got Toronto off to the best possible start, scoring inside of 10 minutes when he pounced on a poor rebound and side-footed into the gaping cage. Marky Delgado nearly doubled with a powerful header, only for it to rebound cruelly off the bar.
Outplayed, New York would be handed a life-line before the break when Bradley Wright-Phillips went down in the area and Daniel Royer converted from the spot.
Drew Moor injured, Nick Hagglund entered and was immense, as was Bono once more, rising to the occasion of his first taste of the MLS Cup Playoffs. Vazquez would be on the receiving end of a crunching challenge that forced him off, but Giovinco would not be subdued, finding the needed breakthrough late, from a free-kick of course, to send Toronto home with the advantage.
One down, four to go.