The Connecticut state tournament series structure has changed several times since the first state tournament was held in the 1950s. Key events in the evolution of this structure include the following:
|1958||After Connecticut leagues are divided into six districts during the early years of Little League Baseball in the state, officials re-draw the state's district boundaries. Ten districts are established, and are numbered sequentially from District 1 in the Stamford/Norwalk area in Southwestern Fairfield County to District 10 in the Eastern portion of the state. All district champions advance to a state tournament, though games are held at local sites within each district until later rounds. The brackets for the state tournament are structured so that Districts 1 through 5 are placed on one side of the draw and Districts 6 through 10 are placed in the other half of the bracket. The practice of splitting the state tournament draw geographically became a permanent feature of the Connecticut state tournament, with only District 9 leagues playing early round games on either side of the draw.
The Connecticut state champion faces the New Jersey state champion in a one game divisional playoff, with the winner advancing to the Eastern Region Tournament.
|1959||District 11 (Eastern Connecticut - Norwich/Putman/Willimantic area) is formed as a spin-off from District 10 (New London area).|
|1968||Delaware and Maryland are moved from the Southern Region to the Eastern Region. As a result, divisional tournament structures are modified. The Connecticut state champion advances to the New England Divisional Tournament, where they face champions from five other New England states for the right to advance to the Eastern Region tournament.|
|1970||The Connecticut state champion advances directly to the Eastern Region tournament when the region tournament's format is expanded to encompass all Eastern Region state champions. Under the new format, the host state receives two berths in the region tournament.|
|1971||New London hosts the Eastern Region tournament, and as a result, Connecticut holds two divisional tournaments rather than a single state tournament. Districts 1 through 5 compete in the Division 1 tournament, while Districts 6 through 11 compete in the Division 2 tournament. The regular state tournament format is re-established the following year.|
|1975||The Connecticut state champion again competes in the New England Divisional Tournament in 1975 and 1976 when the Eastern Region Tournament format is changed to a four-team schedule. Connecticut again advances directly to the Eastern Region tournament in 1977.|
|1987||Little League Baseball chooses Bristol, Connecticut as the site for its new Eastern Region headquarters facility. As a result, the Eastern Region Tournament is held in Bristol annually, and Connecticut again receives two berths in the region tournament.|
|1993||Connecticut begins sending only one representative to the Eastern Region tournament. As a result, the state again crowns a single state champion. Officials establish two double-elimination sectional tournaments, and the two sectional champions meet at the Eastern Region Headquarters facility in a winner-take-all state championship game.|
|1996||The state tournament format is changed to a best 2-of-3 series.|
|1997||Instead of holding the state finals at the A. Bartlett Giamatti Little League Leadership Training Center in Bristol, officials again begin rotating the state championship series to various sites throughout the state.|
|2001||Connecticut is assigned to the New England Region as part of Little League Baseball's expansion of the World Series from eight to sixteen participants.|
|2014||District 12 (far Northeastern Connecticut) is formed as a spin-off from District 11 and portions of Districts 8 and 10. With this new district established, Connecticut officials revamp the state's sectional tournament structure. District champions now advance to three-district sectional tournaments, and the divisional winners meet in a sectional tournament. As with the prior structure, the two sectional champions then meet to determine the state champion.|
|2015||Connecticut officials again revamp the state's tournament structure, and eliminate the divisional round of tournament play. Connecticut's section winners now all advance to a four-team state tournament that determines the Connecticut champion.|
|2022||Connecticut is assigned to the newly created Metro Region as part of Little League Baseball's expansion of the World Series from sixteen to twenty participants.|
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