The Ontario tournament series structure has changed several times since the first provincial tournament was held in the 1950s. Key events in the evolution of this structure include the following:

YEAR	MILESTONE
1957	Ontario's leagues are divided into two districts, with District 1 encompassing the Toronto/Hamilton area and District 2 covering Ottawa and surrounding areas. The two district champions meet to determine Ontario's champion, which then competes against leagues in Western New York as the international tournament progresses.
1958	The Little League World Series expands to an eight-team field. As part of the expansion, the Ontario and Quebec champions face each other in a one-game playoff that determines the Canadian Region representative in the World Series. Western Canada leagues continue to compete in the Western and Northern Region tournament structures, and leagues in Atlantic Canada do not advance past the divisional tournament level until 1963.
1959	District 3 (Lakehead region - Thunder Bay area) is is formed as Little League Baseball spreads to Northwestern Ontario.
1965	The Canadian Region tournament encompasses all leagues in Canada for the first time. As in years past, Eastern and Western Canada both crown champions, but for the first time, these two champions meet for the Canadian Region title. The Stoney Creek Optimist (Ontario) Little League defeats East Trail (British Columbia) 4-0 at Dundas, Ontario, to become the first all-Canada champion. Stoney Creek advances to the championship game of the Little League World Series before falling to Windsor Locks (Connecticut). Stoney Creek's performance represents the highest finish ever by a Canadian league at the Little League World Series.
1966	District 4 (Northern Ontario and the Rouyn/Noranda area in Quebec) is spun off from District 3.
1967	District 5 (Windsor/London area) is spun off from District 1 (Toronto/Hamilton area).
1969	The Ontario provincial tournament uses a double-knockout format for the first time. Galt National Little League rebounds from a loss in the winner's bracket final to win the tournament following three consecutive wins.
1976	For the first time, two leagues from the host district compete at the Ontario Provincial tournament, as both the District 4 champions and a host entry compete in the provincial tournament at Rouyn/Noranda.
1987	District 6 (Ottawa Area - East) and District 7 (Seaway area) are spun off from District 2 (Ottawa Area - West).
2001	Ontario officials use a round-robin format at the provincial tournament for the first time. The top two teams following round-robin competition advance to a winner-take-all championship game. The tournament encompasses only six teams due to the absence of a host league representative and District 5's role as host of the region tournament. The next year, the eight-team tournament again uses a double-knockout schedule.
2002	District 8 (Ottawa River Valley - West) is formed as a spin-off from Districts 2 and 7.

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