The hosts were thumped 3-0 by Atlanta United on Saturday, while the visitors fell to a narrow 1-0 loss against Nashville the following day.
Match preview
Heading into the game on a seven-game unbeaten streak in the MLS, Orlando City were sent crashing back to earth at the Mercedes-Benz Stadium.
In a disappointing performance all round, Oscar Pareja's men were undone by strikes from George Campbell and Ezequiel Barco either side of a Daryl Dike own goal.
The Lions remain third in the Eastern Conference albeit now 17 points behind league leaders New England Revolution but still with two games in hand.
Next up for them is a clash versus an opposing side who have emerged victorious in each of the last four encounters involving the teams.
Thursday's hosts have also failed to find the back of the net in that time which is an area that must be improved on if they are to stand any chance of coming out on top.
Like their opponents, Montreal also had an unbeaten run ended last time out as Nashville inflicted a first defeat in five outings on Wilfried Nancy's men.
Walker Zimmerman opened his account for the season midway through the second half which turned out to be the deciding moment of the contest.
The Canada-based outfit are still hanging on to the last playoff spot in the Eastern Conference but a couple of teams in and around are beginning to bear down on them.
Having picked up just 10 of 31 points coming away from home, Thursday's visitors could do with a better record on the road in their quest to reach the postseason for the second consecutive campaign.
Orlando City Major League Soccer form:
Orlando City form (all competitions):
CF Montreal Major League Soccer form:
Team News
Montreal's trio of Robert Thorkelsson, Ballou Tabla and Lassi Lappalainen remain sidelined with groin injuries and will play no part in Thursday's match.
Bjorn Johnsen could be dropped to the bench for this one as endured another disappointing outing last time out where he was substituted on the hour mark.
Brazilian forward Alexandre Pato continues to nurse a knee injury which has seen him make just one appearance for Orlando City since April.
The home side will also be without the services of 24-year-old Jhegson Mendez who is still a long way off making his comeback from a leg injury.
Orlando City possible starting lineup:
Grinwis; Ruan, Carlos, Jansson, Moutinho; Perea, DeZart, Pereyra; Michel, Nani, Dike
CF Montreal possible starting lineup:
Pantemis; Bassong, Miller, Waterman; Hamdi, Guillard, Wanyama, Choiniere; Mihailovic, Torres, Quioto
We say: Orlando City 2-1 CF Montreal
Both teams are in need of an immediate response to last week's defeat and that should make for an absorbing contest. While we expect goals at both ends, we fancy the home team to just edge their visitors by a narrow margin.