The first month will tell Leafs fans everything they need to know

The Toronto Maple Leafs' first month of the 2026-27 season will tell fans whether or not they are ready to compete or if it's going to be a repeat of last year.

With the regular season set to kick off a month from now, that doesn't mean there's a lot of time left between now, preseason and the start of the year. With four preseason games packed into just two split-squad dates and the regular season starting Sept. 29, Toronto has very little runway to get comfortable before the games count.

They made a series of move that were supposed to make them one of the favourites in the Atlantic Division though there are still questions about whether Auston Matthews can bounce back, if Gavin McKenna can become a key part of the offence, if Morgan Rielly can find some semblance of his old form - and hope that an aging Sergei Bobrovsky is the answer in net.

Luckily for fans, they aren't going to have to wait too long to see if the team is up to snuff considering that the first month of the season has some pretty intense games that could determine whether they are ready or not.

The three contenders Toronto faces before Halloween

Their first game of the season is against Montreal on Sept. 29 and that always leads to an intense matchup. There's going to be a ton of eyes as it's McKenna's debut, and the Canadiens are a team who are no doubt one of the top dogs in the division - it's a tough test right away.

Then as we head into October, the Maple Leafs have two huge back-to-back hurdles to get over. First, on Oct. 8 they play the Vegas Golden Knights on the road, and facing the Stanley Cup runner-ups is always a battle. Then two days later they play Colorado on Oct. 10 - another tough roadblock early on.

If they can prove they are able to withstand the firepower that both those Western teams have, then it will give fans a lot more hope they are ready for what's ahead. Couple that with very winnable games vs. the Senators, the Islanders and Predators and suddenly you could see the Maple Leafs off to a hot start.

Also benefitting Toronto is their weaker end of October, with games against the Blue Jackets, Rangers, Flames, Kraken, and Canucks so if they can ride their momentum early on into a strong October finish then they may be in a much better spot in case things get hairy.

What has to be true by American Thanksgiving

But there are things that have to be solidifed as we finish that first month of the year. Firstly, Auston Matthews has to show that he is back to form and at least putting up consistent points even if he isn't scoring. The goals will come, but if he's showing that his shot is back then it's only a matter of time.

Sergei Bobrovsky needs to show that he can turn back the clock and be the ageless wonder that Toronto is hoping for. They invested heavily in him and he needs to have a very good month to ease any anxiety about his contract.

Gavin McKenna also has to at least show glimpses of what he can do, and while you can't expect him to deliver you the world - a consistent offensive output would go a long way.

Also, the new additions like Colton Sissons, Nick Paul, and Teddy Blueger have to validate John Chayka's decision to rebuild the bottom-six so intently this summer and if there are signs that Toronto is a much smoother and well-oiled defensive machine then it eases more anxiety and makes Chayka look like a genius.

It's a lot to ask from players who are either new, older, or coming off injury but for the Maple Leafs there's no excuse. They invested heavily into this new-look team and only have a couple of seasons to really show the league what they are capable of - and that needs to start as soon as game one.

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