From what I've seen, you need to already have played at least one game against the team. For example, I play for Anaheim, and my season opener is against the Sharks. It is not presented as a grudge match. Several games after I have another game against them, and this time it's presented as a grudge match and I see a dedicated section on the game preview in franchise mode where I see statistics against this team. Also, it seems like it only works against your divisional opponents. My second game against Chicago was a normal game, not a grudge one. That said, your second meeting of the season against the Canadiens should be a grudge match.