[2] Established in 1913 by John William James, the school moved to their current campus at 2365 Bayview Avenue in 1970.

[4][5] The mansion and land were located on part of the Massey family's farm in East York, near Victoria Park Avenue and Dawes Road.

The school operated there until 1969, when the property was sold to developers, who subsequently built the Crescent Town neighbourhood on that site.

By 1970, the school had moved to its current location on Bayview Avenue, which was formerly the estate of businessman Frank Porter Wood.

[citation needed] Crescent teams include basketball, hockey, baseball, track and field, rugby, volleyball, badminton, tennis, swimming, soccer, cross country running, squash, golf and Ultimate Frisbee.

These events were often reported on in the Globe & Mail newspaper; the soccer match between the Crescent School and Appleby College held on November 30, 1937, ended in a tie.

[16] In addition to boxing, soccer, and cricket, the School also held an "annual aquatic gala" where prizes were given to the best boys.