Top 5 Toronto Maple Leafs Moments of 2020-21 Season

TORONTO, ON - APRIL 13: Head coach Sheldon Keefe of the Toronto Maple Leafs watches the action late in the game against the Calgary Flames during an NHL game at Scotiabank Arena on April 13, 2021 in Toronto, Ontario, Canada. The Flames defeated the Maple Leafs 3-2 in overtime. (Photo by Claus Andersen/Getty Images)
TORONTO, ON - APRIL 13: Head coach Sheldon Keefe of the Toronto Maple Leafs watches the action late in the game against the Calgary Flames during an NHL game at Scotiabank Arena on April 13, 2021 in Toronto, Ontario, Canada. The Flames defeated the Maple Leafs 3-2 in overtime. (Photo by Claus Andersen/Getty Images) /
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TORONTO, ON – JANUARY 13: Ben Chiarot #8 of the Montreal Canadiens fights Wayne Simmonds #24 of the Toronto Maple Leafs   (Photo by Claus Andersen/Getty Images) /

No. 4: Opening Night OT Win

An opening night matchup between the Toronto Maple Leafs and Montreal Canadiens is always must-watch TV, but this year, it was even more heightened.

Many people predicted that Montreal would be the best team in the North Division, so it felt like they could be Toronto’s biggest competition in the regular season. Midway through the second period, you could see why.

Montreal was up 3-1 and seemed in control of the game. Instead of waiting a few games to get comfortable, Wayne Simmonds dropped the gloves in his first game as a member of the Leafs and it changed the game.

The Leafs found life after Simmonds’ fight and stormed back to tie the game and eventually force overtime.

After a few minutes of intense 3-on-3 excitement, Morgan Rielly found the back of the net and won the game. That moment was the start of a magical season thus far and was definitely a top-five highlight of the year.