Of the eight were four key schools: These were the early days of Toronto, when the first parliament buildings were established and the first church and jail were constructed.

In fact, it was only fourteen years earlier that Governor John Graves Simcoe arrived at the location on Lake Ontario, home to Mississauga communities[2] and site of important Indigenous trade routes,[3] to lay out the design of the new town he named York.

After the early period 1807-1811, enrolment started at five, rose to twenty, then fell to four - the school gained momentum in 1812 when the redoubtable John Strachan took over as headmaster.

Strachan raised funds for a new two-storey building, completed in 1816 on College Square, a 6-acre (24,000 m2) lot north of St. James' Cathedral, bounded by Richmond, Adelaide, Church and Jarvis Streets.

When Upper Canada College was founded in 1829 it shared a building with the Grammar School and for several years the two organizations were essentially unified.

As the school underwent construction between 1870 and 1871, classes were held in a vacant insane asylum at Queen's Park, where the east wing of the legislative buildings are located today.