|1940||First Schoolboy bonspiel held in Winnipeg; chaired by Ken Watson|
|1947||First all-prairie provinces bonspiel held in Regina|
|1948||Ontario Curling Association (OCA) establishes a committee, chaired by Robert Sutherland of Guelph, to present a plan for Schoolboy Curling in Ontario.
The first Ontario Schoolboy bonspiel (32 entries) is held in Guelph with Imperial Oil and the Gore Mutual Insurance Company donating trophies
|1948-1950||ESSO (Imperial Oil) Trophy awarded to the Championship winner|
|1949-1971||Gore Trophy awarded to the Third Event Winner|
|1950||Sixty-four teams participate in the Schoolboy bonspiel hosted by the Guelph and Galt Curling Clubs|
|1951-1971||ESSO Trophy awarded to the Second Event Winner|
|1951||First Ontario rink competes in the National Championship held in Quebec City with Empire Life Insurance Company as sponsor|
|1952||OCA adopted school curling as part of its program.
Eight divisional winners meet in a straight knock-out competition with the winner advancing to the Dominion Finals
|1952-1954||Crawford Plaque awarded to the Second Event winner|
|1952-1956||Empire Life Trophy awarded to the Champion team|
|1953||Ontario Champions from Oshawa Collegiate & Technical Institute win Canadian Finals in Saskatoon, SK|
|1955-1972||Meisterschraft Trophy to the Fourth Event winner|
|1957-1978||Pepsi-Cola Trophy awarded to the Championship team|
|1957||Ontario Champions from Kingston Collegiate & Vocational Institute win Canadian Finals in Winnipeg, Manitoba|
|1958||All 10 provinces represented at the Dominion Finals; Pepsi-Cola the new sponsor|
|1968||Ontario Champions from Trenton High School win Canadian Finals in Port Arthur (Thunder Bay), Ontario|
|1972-1978||Gore Trophy awarded to the Second Event winner. OCA Award given to the Consolation winner|
|1973||Provincial Finals adopts a double knock-out format.
Ontario Champions from Gananoque Secondary School win Canadian Finals in Moncton, New Brunswick.
Gananoque SS is the only school to have won the Provincial Championships for three consecutive years.
|1978||Last year that Pepsi-Cola sponsored Ontario Provincial Championship.
Last year the Ontario Schoolboy Champion represented the province at the Canadian Finals in P.E.I.
as the Pepsi OCA Juniors competition starts the following year and the Nationals cease to exist.
|1979||Gore Mutual Insurance Company becomes the sole sponsor of Ontario School Curling Championships.
The Gore Trophy is awarded to the Schoolboy Championship team and the Gore Shield awarded to the Schoolboy Second Event Winner.
|1979-1990||The Gore Award is awarded to the Third Event winner|
|1991||Playoff format altered to have the 8 regional finalists seeded into 2 pools.
A 3 game round-robin determined the four finalists to play a modified double-knockout to determine the Provincial Champion and Second Event winner
|1998||Introduction of the Ontario Schoolgirl Curling Championship with the Gore Mutual Insurance Company as sponsor.
The Gore Bowl is awarded to the Schoolgirl Championship team and the Gore Crystal awarded to the Schoolgirl Second Event winner.
|2015||Academic & Community Service Award is established|