Crescent School is founded by J.W. “Jimmy” James to provide a solid education in “…a far gentler place than the fierce caning world” of other private schools at the time. Educating boys in Grades 5 to 8, Crescent’s early locations included 43 Rosedale Road and 76 Collier Street.
Walter Williams becomes Crescent’s second Headmaster. An expanded curriculum introduces music, art and drama ahead of other schools of the day. The House system is inaugurated, with the Greens and the Greys.
Susan Denton Massey generously donates her 40-acre Dentonia Park estate, located in eastern Toronto, to Crescent School.
1935 - 1937
Grades 1 to 4 are added and Crescent School opens to student boarders.
1956 - 1967
A time of transition. Crescent has four Headmasters over a 10-year period: I.S. Carroll, J.S. Buckley, E.E. Senior and W.L. Burridge. The House system is revamped, creating three new houses: Hudson, Mackenzie and Wolfe. Kindergarten and nursery classes are added.
Crescent moves to the current Bayview Avenue campus and C.B. Gordon is appointed Headmaster. The boarding, nursery and kindergarten programs end. Over the next five years, a high school grade is added and the lowest is dropped, until Crescent offers Grades 3–13. Enrolment grows dramatically.
1971 - 1972
The Ladies’ Guild is established, later becoming the Crescent Parent Association (CPA), and Simcoe is added to the House system.
Crescent School wins its first Independent School Athletic Association championship (in soccer).
Crescent School Old Boys’ Association is founded. The “Sons of Crescent” school song is published.
1982 - 1988
John Tansey is appointed Headmaster and school facilities are expanded with the opening of a new gym, library, squash courts, art and music rooms.
1991 - 1997
Cartier and Massey are added to the House system and the science and technology wing is constructed.
2000 - 2008
Geoff Roberts is appointed Headmaster and the Field House, Centre for Creative Learning and Innes Field open.
2010 - 2011
Crescent launches its Great Boys capital campaign with a $30 million fundraising goal and the Lau Family Wing opens.
Crescent School celebrates its 100th anniversary.
Michael Fellin is appointed Headmaster. The Latifi Family Commons and the new Middle/Upper School Library open.
The Great Boys capital campaign is completed, having raised over $34 million.
Crescent launches research initiative, the Crescent Centre for Boys' Education.
Crescent School closes its campus in March due to the COVID-19 pandemic; students transition between in-person and remote learning for 16 months.
Crescent acquires the 7-acre Bob Rumball Centre property at 2395 Bayview Ave.