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|1957||Maryland leagues are organized into three districts, and the three district champions advance to a tournament that determines the state's champion. The Maryland champion advances to the Southern Region Division 4 tournament, where they compete alongside champions from Delaware, Kentucky, Virginia, and West Virginia for a berth in the Southern Region tournament. District 1 includes leagues in Western Maryland, as well as Martinsburg, West Virginia, which at the time was more than 100 miles removed from the nearest West Virginia league. District 2 includes the Baltimore area, and District 3 encompasses leagues on the Eastern Shore.|
|1958||Maryland re-configures its district structure, and splits each existing districts into two districts. The resulting districts are re-numbered 1 to 6 from West to East, and the six district champions advance to a single-elimination state tournament that determines the Maryland champion.|
|1968||Maryland and Delaware are moved from the Southern Region to the Eastern Region. In 1968 and 1969, Maryland's champion competes with winners from Maryland and New Jersey in a Mid-Atlantic divisional tournament, with the winner advancing to the Eastern Region tournament.|
|1970||The Maryland state champion advances directly to the Eastern Region tournament for the first time. The state champion would continue to advance directly to regional competition in every year except 1975 and 1976.|
|1972||District of Columbia leagues compete for the first time alongside Maryland leagues in the Maryland tournament structure. With the exception of 1975 and 1976, any existing D.C. leagues competed as part of the Maryland tournament structure through the 1997 international tournament.|
|1974||District 7 (Southern Maryland) is formed as a split from District 4 (Baltimore Area - South).
Also in 1974, Maryland begins using sectional tournaments to ease travel costs driven by the era's energy crisis. Maryland and D.C. leagues are divided into two sections, and the two sectional winners then meet in the Maryland state championship game. With the exception of 1980, Maryland would use a sectional tournament structure in every year through the 1993 international tournament.
|1981||Maryland officials begin using a double-elimination format for sectional and state tournament competition.|
|1984||District 8 (Lower Eastern Shore) is formed as a split from District 6 (Upper Eastern Shore), and the last remaining charters in the District of Columbia are folded into District 7.
Also in 1984, Maryland revises its sectional structure. State officials arrange the state's eight districts into four two-district sections. Districts 1 and 2, 3 and 5, 4 and 7, and 6 and 8 are paired together in best 2-of-3 sectional tournaments that determine the four teams to advance to the double-elimination state tournament.
|1988||Leagues in District 3 (Baltimore City and County - North) are merged into District 4. New charters are formed in the District of Columbia, and all D.C. leagues north of Bolling Air Force Base are placed in a newly-defined District 3. Sectional structures are revised so that Districts 4 and 5 are paired together in Section 2, while Districts 3 and 7 comprise Section 3. In most years, multiple teams from Districts 3 and 7 advance to the Section 3 tournament due to the relatively small number of leagues in District 3. District tournament losses carry over to sectional tournament play for teams in these districts.|
|1994||Maryland dissolves its sectional structure, and instead begins advancing all eight district champions to a double-elimination state tournament.|
|1998||District 3 (District of Columbia) begins competing as a separate state in the Little League Baseball (ages 10-12) division. In 1998 and 1999, state officials retained the eight-team state tournament field by advancing the host district's runner-up to the state tournament. This practice ended after two years, and the tournament reverted to a seven-team, double-elimination format.|
|2001||Maryland is assigned to the Mid-Atlantic Region as Little League Baseball expands the Little League World Series from eight to sixteen participants.|
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