All three teams in the group are still in with a chance of making it through to the knockout stages heading into this one, and there is all to play for in Ontario.
Match preview
Having not featured in the opening gameweek, Pachuca kicked off their cup journey with a penalty-shootout victory over New York Red Bulls at Estadio Miguel Hidalgo on Wednesday.
Like in the 2-0 defeat to Pumas prior, Guillermo Almada's men were guilty of being lethargic in possession before going behind to Elias Manoel's strike, after which Salomon Rondon levelled matters to send the game to spot-kicks.
Failure to get the job done in 90 minutes saw Los Tuzos pick up just two points from their opening triumph to currently sit joint-top of Group 14.
Progressing into the next phase of the Leagues Cup could serve as a catalyst to turn what has been a disappointing domestic campaign to date around.
Pachuca have managed just four points from as many outings this term, and that can majorly be attributed to their attacking woes as they have failed to score in three of four league outings so far.
Like Pachuca, Toronto also needed penalties to see off fellow MLS outfit New York Red Bulls in their opening cup involvement at the Red Bull Arena on Sunday.
Off the back of seven straight defeats between mid-June and early July, John Herdman's men have now won three of the subsequent four games across all competitions.
The Reds have also kept consecutive clean sheets for the first time since April which bodes well ahead of two cup clashes in the space of three weeks either side of a league game against Houston Dynamo.
Having bowed out early in last season's Leagues Cup, Toronto will be wary of another group-stage exit in front of their fans, who have seen them lose four of the last five home encounters.
However, Monday's hosts can afford to play with a bit of pressure off their backs as a draw also guarantees them safe passage into the round of 16.
Pachuca Leagues Cup form:
D
Pachuca form (all competitions):
W
L
D
W
L
D
Toronto Leagues Cup form:
D
Toronto form (all competitions):
L
L
W
L
W
D
Team News
Brandon Servania remains out of action for Toronto due to a knee injury which has sidelined him since the back end of last year.
The home side will also be without the services of 23-year-old Tyrese Spicer, who is still nursing a back injury.
Off the back of yet another underwhelming display last time out, Prince-Osei Owusu has now scored just once in 11 outings leading up to this one, but the forward is expected to feature here nonetheless.
Pedro Pedraza was forced off with an injury scare in Pachuca's win over New York Red Bulls, making the 24-year-old a doubt for this one.
Salomon Randon is definitely one to keep a close watch on here having found the back of the net in seven of his last nine starts for club and country.
Pachuca possible starting lineup:
Moreno; Rodriguez, Cabral, Barreto, B Gonzalez; A Gonzalez, Deossa; O Gonzalez, Bautista, Idrissi; Rondon
Toronto possible starting lineup:
Johnson; Petretta, Long, Gomis; Laryea, Florea, Osorio, Bernardeschi; Insigne, Etienne, Owusu
We say: Pachuca 0-1 Toronto
Given what is at stake here, we are expecting a cautious game with neither side committing too much in attack.