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|1950s||Montana's first Little League charters are established in the early 1950s, and the state's leagues first enter the international tournament in 1952, when three leagues from Billings and two from Butte compete as part of the Region 8 tournament structure. Billings' Lissa Little League finishes tops among these Montana leagues, and advances to a sectional tournament in Richland, Washington, where they compete alongside leagues from other states and provinces in the Pacific Northwest. Through 1956, Montana leagues are funneled against leagues from other Western states in multi-state area and district tournaments, as the number of charters, though rapidly growing, was relatively low during this era.|
|1957||Montana's first state tournament is held, as five leagues from the Billings area meet to determine the state's first champion. Rimrock Little League edges the Mustang Juniors Little League, 9-8, and advances to a sectional playoff against the Wyoming state champion. This winner then advances to the Western Region Division 1 tournament. Montana's champion would continue to face other state champions from Mountain and Pacific Northwest states until the early 1970s.|
|1961||As the number of leagues in Montana grows, the state is divided into two districts, with District 1 covering Eastern Montana, and District 2 encompassing Western Montana. The two district champions meet in a one-game playoff that determines the state champion.|
|1971||Montana's champion begins advancing directly to the Western Region tournament rather than first competing in a divisional tournament. Montana's champion has continued to advance directly to regional tournament competition in every year since this time.|
|1982||Montana officials use a best 2-of-3 format at the state tournament for the first time.|
|2001||Montana is assigned to the Northwest Region as Little League Baseball expands the Little League World Series from eight to sixteen participants.|
|2022||Montana is assigned to the newly created Mountain Region as Little League Baseball expands the Little League World Series from sixteen to twenty participants.|
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