In their final domestic encounter before this tournament, the Lions earned a 1-1 draw against New York City FC, while Le CFM were beaten 1-0 by arch-rivals Toronto.
Match preview
There has been a resurgence of sorts for Orlando City this month, with this team unbeaten in five consecutive MLS fixtures in July.
Four of those games ended with a victory for Oscar Pareja's men, who have climbed up to seventh in the Eastern Conference table, seven points above the playoff line.
Orlando City are unbeaten in their last three matches played at Inter & Co Stadium, outscoring their three opponents by a combined margin of 10-3.
Friday will be their fourth home match all-time in this competition, with the Lions losing only one of those encounters in 2021 versus Santos Laguna (1-0).
The Lions have conceded the opening goal in every one of their Leagues Cup fixtures but came from behind to earn a result in both of their group games last year.
This will be the third time they face an MLS opponent in this competition, and Orlando failed to win the two previous meetings, with Inter Miami eliminating them in the round of 32 last year (3-1).
With points in three of their previous four games, Montreal are back in the mix for a post-season berth in the MLS Eastern Conference.
Coming into this tournament, they are a point behind Atlanta United for that final playoff spot with nine regular-season games remaining.
Le CFM have never played a Leagues Cup fixture on American soil, with both of their group games last year taking place at Saputo Stadium.
Playing away from home has been an issue for them throughout the year, with Laurent Courtois's men winless in their last 11 matches across all competitions.
They have a chance on Friday to win a Leagues Cup contest within 90 minutes for the first time, squandering a 2-0 lead in their opener last year against Pumas before winning on penalties.
Montreal are winless in their last four away matches against Orlando City, failing to score in three successive trips there.
Orlando City form (all competitions):
L
W
W
W
W
D
CF Montreal form (all competitions):
W
L
D
W
D
L
Team News
In their draw with NYCFC last weekend, Orlando were missing Mason Stajduhar, who will not be back this season because of an injury, while Michael Halliday is dealing with a sore knee.
Duncan McGuire is away on international duty, currently representing the United States national team at the Olympics in Paris.
A 52nd-minute strike by Ramiro Enrique ultimately was not enough last week, with New York City equalising five minutes later.
On Saturday, Logan Ketterer was sidelined for Montreal with a sore ankle, Lassi Lappalainen has a groin injury and Mason Toye was sold to the Portland Timbers.
Four new faces were in their starting 11 against Toronto, including Samuel Piette, Raheem Edwards, Jules-Anthony Vilsaint and Josef Martinez.
The only goals they scored at this tournament last year came courtesy of Bryce Duke and Mathieu Choiniere in their shootout victory versus Pumas.
Orlando City possible starting lineup:
Gallese; Thorhallsson, Schlegel, Jansson, Santos; Araujo, Cartagena; Lodeiro, Ojeda, Torres; Enrique
CF Montreal possible starting lineup:
Sirois; Waterman, Alvarez, Sosa; Ruan, Choiniere, Piette, Edwards; Vilsaint, Lassiter; Coccaro
We say: Orlando City 2-2 CF Montreal (Orlando City wins on penalties)
Nine of the last 10 meetings between these two teams have seen multiple goals scored, and we expect an entertaining affair on Friday, with the difference perhaps being the shot-stopping ability of Orlando's Pedro Gallese.