Maple Leafs Season Preview: Six Questions That Decide the 100th Season

The Maple Leafs season preview starts with the worst year in a decade

Any honest Maple Leafs season preview for 2026-27 has to begin where the last one ended: 32-36-14, 78 points, eighth in the Atlantic Division and 15th in the Eastern Conference. Toronto scored 253 goals and allowed 299. It was a 30-point collapse from the 108-point season before it, the steepest single-season decline in franchise history.

Then the organization tore itself down. Brad Treliving was fired. John Chayka was hired as general manager in May with Mats Sundin brought in as a senior executive adviser. Craig Berube was dismissed May 13 and Jim Hiller took the bench. Toronto won the draft lottery and selected Gavin McKenna first overall.

The team that opens the 100th season under the Maple Leafs name on Tuesday has nine players making their Leafs debut. Here are the six questions that actually determine where this ends.

1. Is Auston Matthews healthy, and what does healthy even mean now?

Matthews had surgery on March 19 to repair a Grade 3 MCL tear in his left knee, a 12-week recovery. He said during camp that he had not been fully healthy for the previous two seasons — the first public explanation for a scoring decline that had spawned a hundred theories.

The camp evidence is encouraging without being conclusive. He posted three points in the pre-season finale and his skating speed has been tracked back near his pre-injury range. A chiropractor who works with him said publicly he was on track with no expected delay.

The honest uncertainty: Matthews is 29 and has now had two seasons compromised by injuries he played through. A healthy Matthews is a 50-goal player and Toronto's single largest swing factor. A Matthews managing something again is a 35-goal player on a team that cannot afford one.

2. Can Sergei Bobrovsky be a starter at 38?

Chayka's signature summer signing was a 38-year-old goaltender, which is either shrewd or reckless depending on whether you weigh the two Stanley Cups in Florida or the actuarial tables. Bobrovsky's conditioning reputation is genuinely exceptional, and the club appears to be planning on 40 to 50 starts.

Anthony Stolarz is the other half of the tandem, under contract through 2029-30, and is coming off a season everyone in the organization hopes was an anomaly. Public projection models have been brutal on this crease, ranking Toronto near the bottom of the league in expected goals saved above average.

Those models are also the same ones that consistently undervalue veteran goaltenders with elite technical foundations. This is the projection Toronto most wants to be wrong about.

3. Does the defence give back what the goaltending saves?

Toronto allowed 299 goals last season. That number is not primarily a goaltending failure — it is a structure and personnel failure, and the personnel did not fundamentally change.

Darren Raddysh arrived and is effectively the No. 1 right-shot defenceman. Oliver Ekman-Larsson is a good bottom-pair defender who was asked to be a top-four player. Jake McCabe is a very good second-pair defenceman playing above his level. Chris Tanev is 36 with a body that has absorbed a decade of shot blocks. Morgan Rielly is still here after a summer of trade speculation that never produced a serious offer.

That is a group where everyone is one slot too high. Over 84 games, that compounds.

4. Is there a third-line centre on this roster?

Colton Sissons is penciled in behind Matthews and John Tavares, with Teddy Blueger on the fourth line. Sissons is a legitimate NHL defensive centre and a genuinely useful penalty killer. He is not a player who drives a line.

The Leafs have been trying to solve this position since Nazem Kadri left, and the 84-game schedule with 28 divisional games makes it more acute, not less. Against Florida and Tampa Bay four times each, a third line that cannot survive matchup minutes is where games get lost.

Chayka has been linked to centre solutions all summer without pulling a trigger. The internal case for a trade is real, but so is the cap constraint — Toronto is compliant only through Max Domi's LTIR placement.

5. How fast does Gavin McKenna become a difference-maker?

McKenna produced 51 points in 35 games as a Penn State freshman and was a Hobey Baker top-10 finalist at 18. He is going to be a star. The question is timing.

He projects onto the second line with Tavares and William Nylander, which is the correct place for him — two veterans who can win pucks and carry the neutral zone while he finds open ice. If he produces 45 to 55 points as a rookie, Toronto's top six is suddenly legitimate. If he needs a year, the second line is Tavares at 36 and Nylander carrying an 18-year-old.

The nine-game window before his entry-level contract burns a year arrives in mid-October. That decision is the first real test of Chayka's patience.

6. Can Jim Hiller actually change how this team defends?

Hiller got a 13-day training camp and four pre-season games — the shortest runway of any new NHL coach this year, courtesy of the new CBA's compressed calendar. He is installing a system on a roster with nine new players.

The stated emphasis in camp was on defensive-zone retrievals, forecheck structure and giving Matthews more offensive-zone freedom. Those are the right priorities. Whether they hold up in November, when the schedule tightens and the injuries start, is the actual test of the hire.

Coaching changes produce the largest measurable effects in two places: special teams and defensive-zone exits. Watch the penalty kill. If Toronto's PK is still below league average in December, Hiller's system did not take.

Where this realistically lands

The projection consensus is unkind. Public models have Toronto around 91 points with roughly 37 per cent playoff odds. The Hockey News picked them fourth in the Atlantic. Most previews put them behind Florida, Tampa Bay, Montreal and Boston with Ottawa and Buffalo in the same tier.

Our read: that is roughly right, and the distribution is wide. This is a team with a genuine path to 95 points if Matthews is healthy, Bobrovsky holds up and McKenna produces immediately — and a genuine path to 80 if two of those three break the wrong way. There is very little in the middle, because the roster has almost no depth to absorb a failure at the top.

Toronto's most likely outcome is a wild-card race decided in the final two weeks. For a fan base that spent a decade with playoff appearances treated as a formality, that is the new baseline.

What's next

The Leafs open Tuesday at Scotiabank Arena against Montreal at 7 p.m. ET on Sportsnet, the first of 84 games and the second of 28 divisional ones. The scouting report on the Canadiens is here.

The early schedule matters more than usual in a balanced format. Points banked in October against divisional opponents count exactly as much as points in March, and Toronto cannot afford to spend two months finding itself. Follow the standings from night one and track the roster here.