The third and final meeting will be played on Wednesday night at BMO Field, a match rearranged to accommodate TFC's friendly against Liverpool and Chicago's against Aston Villa back in July.
On the verge of official playoff elimination, Toronto, depleted though they may be, will look to see out the remaining fixtures on the calendar with an eye towards building to the future - once again, sigh.
It's been slightly more than a month since the two last met - much of what was written before still rings true (Meeting the Second) - but a closer look at the Fire is in order.
A 2-1 win over Toronto at Toyota Park on August 4th began a strong run of form for Chicago.
A pair of further wins - at Philadelphia 1-3 and 2-1 home to New England - were followed by a 4-2 loss at DC - on short rest it must be said, before a 3-1 win over Houston saw them enter the break securely fixed in playoff contention, currently fourth place in the East.
With eight matches remaining, a win in Toronto could see them launch themselves up the table into second place, within striking distance of conference leaders Kansas City.
Much of Chicago's recent success has revolved around the goal-scoring prowess of Chris Rolfe, the return to health of Arne Friedrich to solidify the back-line, and the integration - and increasing comfort therein - of Sherjill MacDonald and Alvaro Fernandez into the starting eleven, as well as the impressive spot duty from Daniel Paladini in place of injured captain Logan Pause.
In fact, the new acquisitions have so easily taken to the side that the decision was made to allow Marco Pappa to joined Dutch side SC Heerenveen early, rather than waiting until January as previously agreed.
Coach Frank Klopas has stuck to the 4-2-3-1 formation that has seen the Fire quietly put together a very impressive campaign; flying under the radar of the mainstream with more high-profile sides - New York, Kansas City, Houston, DC - occupying the spotlight.
The projected lineup is as follows: Sean Johnson in goal; from right to left - Jalil Anibaba, Arne Friedrich, Austin Berry, and Gonzalo Segares across the back; Daniel Paladini and Pavel Pardo at the base with Alvaro Fernandez, Chris Rolfe, and Patrick Nyarko across the midfield; and Sherjill MacDonald as the lone striker atop the formation.
The return of Pause in the final five minutes against Houston - from pneumothorax and a couple of broken ribs suffered against Philadelphia - could see him return to the starting lineup, but given the need to build fitness and the impressive form of Paladini - including two goals in his three starts - there is little cause to rock the boat.
Speedster Dominic Oduro has largely been relegated to the role of substitute, from which his blistering pace poses a real threat to tired defenders.
Brazilian attacking mid Alex too, has found his playing time limited and largely from the bench of late.
Young midfielders Michael Videira and Corben Bone made their first starts of the season in Sunday's 2-2 friendly draw with Club Santos Laguna and both scored in the second half as the Fire came back from a two-goal deficit.
Nineteen year old homegrown product Victor Pineda also started against the Mexican Champions and by all accounts was impressive. He could be in line for some minutes.
A negative portent began the occasion with Oduro flicking a header into the path of Rolfe peeling off the shoulder of Logan Emory in the first ten minutes. In alone one-on-one, Milos Kocic stood strong in the face of Rolfe's pressure to deny the chance, only to take a clattering as Doneil Henry's knee struck his face and Rolfe stepped on his stomach.
Not the way to begin a calm and controlled evening.
Toronto took the lead very much against the run of play in the sixteenth minute when Ryan Johnson pounced on a weak Pappa back-pass from the left-flank. Johnson ran onto the loose ball, moving infield from the attacking right and waited from his namesake in goal to commit before lifting a finish neatly over him with his left-boot.
Pappa made up for his error twenty minutes into the second half, latching onto a failed Henry clearance that bounced off the instep of Emory into the path of the Guatemalan attacker at the right-post. Pappa rounded Kocic in goal before drawing Richard Eckersley off the line and slotting a left-footed finish past him into the open, near-side.
Emory was dismissed for a second bookable offense after eighty minutes. His first card came for blocking off the run of Oduro in transition in the fortieth and the second for preventing the turn of Rolfe with an aggressive boot on the halfway line.
Under pressure as Chicago pushed for an equalizer, Jeremy Hall was called for a mystery foul in which he was injured and could not continue. Having burned all three subs, Toronto was forced to play out the match with nine men.
Pardo took the ensuing free kick from the left-flank, swinging the ball towards the back-post, where it was met by Berry with a towering header back across the keeper to the left-side of the goal.
Their speedy counterattack potential, the constant threat of shots from distance, and their aerial ability from set-pieces has combined to make Chicago a dangerous and potent attacking force.
Whether Friedrich - scored vs. Philly from a corner kick, Berry - against Toronto from a free kick - or even full-back Segares - from a free kick against DC, not to mention the one he nabbed against Toronto the first time they played - dead-ball situations must be considered carefully. Either mark up well or limit the opportunities.
Segares, in particular, is a difficult man to account for; it is unusual for an outside back to be involved in attacking set-pieces - they usually stay back in midfield to brace for a potential counterattack - but not so for the Costa Rican.
Watch how completely unmarked he is against DC at the back-post here.
Chicago can be vulnerable - as with all MLS-level defenses - from set-pieces themselves. Watch the marking on this Brandon McDonald goal; woeful.
Sean Johnson, as mentioned in the previous preview, can be spectacular, but spotty.
This Macoumba Kandji goal was ruled off - incorrectly - for a supposed handball, but is a perfect example of how not to deal with a low cross into the corridor of uncertainty. That mistake, popping it up to the attacker, could drastically have altered that match.
Toronto must be wary of shots from range; whether Rolfe's feathered attempts - as against San Jose, Paladini's late runs to the top of - or into - the box or Alex's spectacular goal against Houston.
Anibaba has a decent long throw on him.
An interesting aside to those fretting over Toronto's possession and passing statistics and their relevance in winning in MLS - have a look at the statistics from Chicago's recent 3-1 home win over Houston, despite being out-possessed (67.4 to 32.6) and out-passed (582 to 274); clearly the most important measure of any match remains chances converted.
Chicago Fire Fourth Place Eastern Conference
Played 26 Points 44 Wins 13, Draws 5, Losses 8
Goals 35 Against 31 Difference +4
Home 9-2-2 (+8) Away 4-3-6 (-4)