The Bombers, 1-4, can pull into a tie with the 2-3 Alouettes with a victory, as they play only their second home game this season.
The Alouettes are looking to turn around their worst season start since 2008 and avoid sharing the league's cellar with last year's East Division champions.
"You always want a victory to enjoy that bye week," says veteran Montreal quarterback Anthony Calvillo.
"That's the situation we're in now and I'm sure Winnipeg is telling themselves the exact same thing. It'll be a challenge."
Their task wasn't made easier by a 12-hour wait at Trudeau Airport in Montreal after their scheduled 8 a.m. flight to Winnipeg was delayed Thursday. They arrived at the airport at 6:30 a.m. and didn't board the plane until nearly 6:30 p.m.
"Brutal day,'' kicker Sean Whyte said on Twitter.
While Montreal may be struggling, with Calvillo in charge the Bombers know their second win isn't going to be any easier than their first against the Edmonton Eskimos.
But they do have a plan to deal with the wily veteran, now in his 19th CFL season, says linebacker Jonathan Hefney.
"We're just going to go out and play hard, go out and try and put pressure on him and try do what we can do with their receivers and we'll see what happens," he said this week.
"I feel we didn't put enough pressure on him last time so we're going to work to get that done."
When they met July 6 in Montreal, the Bombers let the Alouettes get 14 unanswered points in the first quarter and another 14 in the fourth on the way to a 41-30 victory
"We just want to make him be rattled," says Hefney.
"Get to him as fast as we can. He gets rid of the ball fast, that's why he don't give up a lot of sacks, so we're just going to try to get to him as close as we can."
Calvillo has his own plans.
"We have to make sure we take care of the ball early and that we put some points up on the board because you know their crowd is going to be loud," he predicted.
With close to 30,000 in the stands against Edmonton, the roar was deafening.
Winnipeg's offence will be led for the second time this year by Alex Brink as a starter. Buck Pierce is out with an injured foot.
The 23-22 win the Bombers eked out last week against Edmonton did a lot to lift the team's spirits during practice this week.
It was big for Brink, who tanked during his first start in Toronto the week before when he completed only nine of 34 passes as the Bombers bowed 25-22 to the Argonauts.
"It's definitely a confidence builder. You take your successes and you want to build off them," he said this week.
"Guys want to see a quarterback that can lead them to victories."
He has the CFL's top receiver so far this season — Chris Matthews — and recently returned tailback Chad Simpson to help keep the team on a roll. They had a touchdown each against Edmonton.
Montreal coach Marc Trestman knows Simpson is dangerous.
"We've got to keep an eye on him," he says.
"They've been throwing the ball extensively, more than 70 per cent on first down, but the times when he does run he's scary."
The injury bug continues to bite both teams.
Winnipeg backup running back Nathan Riva and fullback Jordan Matechuk both hurt in practice this week.
That leaves the Bombers fresh out of backup Canadian tailbacks so they dipped into the practice roster for import Will Ford to back starter Simpson. Ford was only signed as a free agent last month.
It means some juggling for coach Paul LaPolice as he adds one import and removes another to keep his ratio in check, in this case linebacker Terrell Parker.
"It tightens your specials teams a little bit but certainly when you've lost three Canadian running backs there's not much you can do," he said. "We've made adjustments."
Ford is happy for the shot and has been taking plenty of first-team reps during practice.
"Yesterday I took all of them so it was a little rough on me but I'm pretty much in tune," he said mid-week.
Montreal defensive tackle J.P. Bekasiuk will be lost for at least a month with a knee injury and kick returner Trent Guy is out with a rib injury. Victor Anderson and Bo Bowling will handle return chores.
"He said he would be hurting the team if he had to play," Trestman said of Guy.
"With the bye week, hopefully we'll see him next time around."