High on the rotation was a favourite for Blues fans, the 1999 preliminary final, when Carlton pipped the Bombers by one point thanks to Fraser Brown's inspirational tackle on Dean Wallis in the dying seconds.
"We watched highlights of that game to just try to point out to the guys what it really means to be part of one of these clashes rather than it being just another game for them," Montgomery said.
During the week, senior coach Brett Ratten put a special emphasis on what it meant to play for Carlton against Essendon, who can both lay claim to being the most successful of the VFL/AFL clubs with 16 premierships apiece.
Clashes between the Blues and Bombers in recent years have thrown up some great contests, with three games decided by less than two goals and one an agonising draw.
And it's obvious to Montgomery why both sides fight so hard.
"I think the two clubs hate each other and they fight tooth and nail to make sure that every ball is a massive contest and a real scrap," he said.
"Brett has made it a huge focus this week on that rivalry between the two clubs, he has gone back in years and shown footage of the epic games between the two clubs and why there is real rivalry there.
"He's really put something in place based on history."
Montgomery said the test for Carlton would be whether they could respond from last week's 40-point defeat to St Kilda and post its first win of the season.
Ratten's messages clearly struck a chord with the former Western Bulldogs and Port Adelaide player, who joined Carlton's coaching staff following his retirement last year.
"Coming from two smaller clubs in the Doggies and Port you don't get a real appreciation for the rivalry," Montgomery said.
"You understand it while you're growing up being a football spectator or enthusiast that these games are big, but you don't feel it until you get in the four walls how much it means to them and how much they do hate each other.
"So it's been a real eye opener for me as well."
The views in this story are those of the author and not necessarily those of the clubs or the AFL.