Toronto Maple Leafs vs Montreal Canadiens Prediction: NHL Opening Week Picks (Sept 29, 2026)

By Cole Gallagher / August 23, 2026

The oldest rivalry in the National Hockey League opens the 2026-27 campaign at Scotiabank Arena, and Canadian bettors could not ask for a better first night. Toronto host Montreal on opening night of an expanded 84-game season, with the added possibility that Gavin McKenna, taken by the Maple Leafs with the No. 1 pick in the 2026 NHL Draft, makes his NHL debut in the loudest building he could have drawn. Here is the full top betting sites breakdown for the game, part of our ongoing NHL opening week coverage.

Odds Comparison

Team Analysis

Toronto Maple Leafs

Toronto open at home with the sort of night the franchise builds its calendar around: Montreal in the building, a full house and the prospect of introducing the No. 1 pick in the 2026 NHL Draft. Gavin McKenna’s status for the opener is the storyline that will dominate the pregame, and whether he draws in or watches from the press box, the Leafs are still leaning on an established top-six that can score in bunches. The question that follows this team every autumn is whether the defensive structure and goaltending hold up when the game tightens in the third period.

Key Storyline: Gavin McKenna, the No. 1 pick in the 2026 NHL Draft, could make his NHL debut against Montreal on opening night

Montreal Canadiens

Montreal walk into the loudest possible road environment to start their season, and this rivalry has never needed standings context to produce a hostile 60 minutes. The Canadiens have built around speed and a young core, which plays well in October when opponents are still rounding into shape and legs matter more than systems. Getting through the opening ten minutes without conceding, and taking the crowd out of it, is the entire road blueprint here.

Key Storyline: Montreal’s young, fast forward group tries to silence Scotiabank Arena early in the oldest rivalry in the league

Key Betting Angles

Leafs-Habs games rarely follow the script the standings suggest, and season openers add another layer of noise. Both teams will be pushing pace, neither penalty kill has meaningful reps together yet, and rivalry games historically draw more trips to the box than a neutral fixture would. That combination points at the over more often than not, and it makes the puck line a risky place to be on either side of a game that has produced an unusual number of one-goal finishes.

We are tracking the full NHL opening week slate, plus everything else on the board, over on worldcupbetting.ca.

Our Prediction

Cole’s Pick: Toronto Maple Leafs moneyline

Home ice in this rivalry is worth more than it is almost anywhere else in the league, and Toronto’s top-end forward talent is the most reliable thing on the ice in a game where systems will be loose. Montreal have the speed to hang around and the crowd will get nervous at some point, but the Leafs should have enough finish across three periods. Do not be surprised if this needs overtime.

Confidence: medium, opening-night rivalry games are volatile and Montreal are quick enough to steal one on the road

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Cole Gallagher

Cole Gallagher covers soccer betting for WorldCupBetting.ca, specialising in match predictions, odds analysis and tournament futures. Based in Toronto, he has followed the Canadian men’s national team since their 2022 qualifying campaign and brings a line-shopping, data-first approach to every pick.