[thecharioteer]

Government House 1900 (King and Simcoe; St. Andrew's behind):

Old Upper Canada College, 1860:

 

[Red October]

Are you sure the bottom picture isn't also of the Parliament Buildings on Simcoe? They look like a different angle of this:

http://en.wikipedia.org/wiki/Ontario_Legislative_Building#Early_structures

 

[thecharioteer]

Very similar, Red October, but this early watercolour of UCC (TPL) clearly shows similar massing:

 

[Red October]

Ah, good point, thanks.