Toronto Maple Leafs vs Montreal Canadiens 29 September 2026 Prediction

Toronto held the first overall pick in the 2026 draft and enters the season among the Stanley Cup contenders. The Maple Leafs open the regular season against fellow Original Six team Montreal, which has strengthened its roster around a young core led by Ivan Demidov, Cole Caufield and Juraj Slafkovsky.

Bobrovsky Joins Toronto

Sergei Bobrovsky, a frequent obstacle for Toronto over the past two seasons, is now with the Maple Leafs. The Russian goaltender won back-to-back Stanley Cups with Florida. In a recent preseason game, Jim Hiller’s team beat Ottawa 6-1, and Bobrovsky made 13 saves.

Toronto fans will also be watching Gavin McKenna, the club’s first overall pick in the 2026 draft. He recorded an assist in the preseason after putting up 51 points, including 15 goals and 36 assists, in 35 NCAA games last season.

Toronto Maple Leafs Predicted Lineup: Bobrovsky (Akhtyamov); Tanev, McCabe; Roslovic, Matthews, Knies

Other Players: Defensemen: Raddysh, Rielly, Stecher, Ekman-Larsson; forwards: Nylander, Tavares, McKenna, Sissons, Koblar, Cowan, MacEwen, Grul, Pezzetta

Out/Questionable: Domi (injured); Joshua and Paul (both questionable)

Manager: Jim Hiller

Montreal’s Strong Preseason

Montreal has been among the Eastern Conference’s top teams over the past two seasons. Last season, Martin St. Louis’s team reached the Eastern Conference Final, where it was swept by eventual Stanley Cup champion Carolina. The Canadiens will look to go further this season.

Montreal won four of its five preseason games. Its only loss was a 4-3 road defeat to Ottawa. The Canadiens also beat Ottawa 4-2 at home that same day. Slafkovsky had a goal and two assists, scoring the game-winner midway through the third period.

Montreal Canadiens Predicted Lineup: Dobes (Fowler); Carrier, Hutson; Kreider, Suzuki, Caufield

Other Players: Defensemen: Xhekaj, Struble, Matheson, Dobson; forwards: Newhook, Evans, Slafkovsky, Bolduc, Dach, Berard, Pastukhov, McCown, Texier

Out/Questionable: Guhle (injured); Demidov and Kapanen (both questionable)

Manager: Martin St. Louis

Toronto Has Struggled Against Montreal

Montreal has won the last five meetings between these teams. That includes two games in the 2026-27 preseason: a 4-1 win in Ontario and a 4-3 overtime win in Quebec. Demidov scored in the home game.

Key Trends

Toronto scored a power-play goal in each of its four preseason games.

The Maple Leafs scored in the second period of every preseason game.

Montreal allowed a power-play goal in four of its last five games.

Toronto Maple Leafs vs Montreal Canadiens Prediction: Montreal Canadiens Moneyline at 1.88

Main pick: Montreal has won five straight meetings with Toronto, including its last two games in Ontario. The Canadiens also won four of five preseason games, while the Maple Leafs lost two of four. The pick is Montreal Canadiens moneyline at 1.88. Projected score: Toronto 2, Montreal 4.

Goals pick: Montreal scored at least four goals in four of its five preseason games. Toronto allowed more than two goals in both meetings since the summer break. The pick is over 5.5 total goals at 1.67.