The Maple Leafs’ newly released 2026-27 schedule has already done more than fill in dates. It has put a few familiar names back on the calendar, and Toronto fans now know exactly when some old faces will roll back into town.
The season opens Sept. 29, but the first date that jumps off the page for plenty of Leafs supporters is Dec. 3, when Sergei Bobrovsky returns to Florida as a member of Toronto. After the offseason move, the pressure is obvious. At $7-million per year for a soon-to-be 38-year-old, the expectation is that Bobrovsky can justify the price tag, and Florida is the kind of opponent that will make that conversation loud fast.
There is also a pretty eye-catching history there. Bobrovsky’s career line against Florida sits at 13-1-2 with a 1.94 GAA and .940 SV%, which gives Toronto every reason to believe it added a goalie who has already had the Panthers’ number. If he can walk back into Florida and shut them down again, it would be exactly the sort of statement the Maple Leafs are paying for.
A few days earlier, Toronto will see another former goalie back in the building when Joseph Woll returns along with Simon Benoit. Woll’s exit came in a trade before the draft for Samuel Ersson, Emil Andrae and a draft pick, and he now projects to form a strong 1-2 tandem with Dan Vladar, who recently re-signed for the next few years.
Woll’s Toronto run had its highs and lows, but he was still a popular figure around the team. He finished with a 63-43-9 record, a 2.94 GAA and .906 SV%.
The concern now is less about memory and more about what happens if he looks sharp against his old club. If he comes in and keeps Toronto’s offence quiet while staying healthy, that will make the decision to move on from him feel a lot harder to defend, especially after his recent injury issues and his rough showing at the IIHF World Championships.
Then there is Nick Robertson, whose return arrives in 2027 and might stir up the most complicated reaction of all. Fresh into a new deal and now with Pittsburgh, Robertson comes back as one of the more polarizing former Leafs in recent memory. He was productive enough to tease bigger things, but never quite found that next level.
His career-high 16 goals last season was a step, but the bigger picture still leaves questions. Robertson has 88 career points and has only just reached the 30-point mark, which is a long way from what Toronto hoped for from a second-round scorer. He could have plenty of motivation when the teams meet, and while he may get a mix of cheers and boos, the real story is what might have been.
For Toronto, the schedule has turned a few regular-season dates into checkpoints. Bobrovsky, Woll and Robertson are all coming back, and each one brings a different kind of test, memory and what-if with them.
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