1960's Toronto was ambitious.. but not 300+m ambitious for anything real. The most ambitious project of the era was CN Rail's planned redevelopment of it's downtown rail yards, which at it's centrepiece was to be a large new communications tower, the tallest in the world. The project would have demolished Union Station and developed large residential, office, hotel, and commercial spaces, including a convention centre.
Of the project, only the Convention Centre and CN tower got built. The rest got cancelled.
An early vision of the project: Notice that the communications tower has a 3-prong design which is significantly different than what ended up getting built.
Later versions of the proposal retained the central portion of Union Station:
a better view of the original design for the CN tower:
The final version before cancellation, showing the CN tower looking closer to how it was built:
The only "real" cancelled supertall in Toronto was from the 1990's when Loblaws proposed a supertall at Yonge and the 401 in suburban North York for their HQ (called "Wittington Place"). The proposal at the time also included a 20,000 seat arena to be the home of the Toronto Raptors, prior to the construction of the Scotiabank Arena downtown. At the time the Raptors and Leafs were under seperate ownership and were planning seperate arenas - The Leafs were about to start construction on their rink directly over Union Station before last minute buying the Raptors and taking over the Scotiabank Arena project, which had evolved after the cancellation of the Wittington Place project.
It would have featured a 57 storey office building with large spire, designed by Arthur Erickson..
The largest buildings not to be in the downtown core of Toronto were an early version of the Eaton Centre, which would have demolished old City Hall (notice a theme here?):
And the cancelled Bay Adelaide Centre of the 1980's, which was actually partially built with it's concrete core sticking several floors out of the ground for 2 decades after cancellation (On the left of the image):
None were supertalls though.