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| Year | Milestone |
| 1948 | One year after the first Little League national tournament is held, Little League Baseball expands into Virginia. A league from Alexandria is invited to compete in the second annual national tournament, where they dropped an opening round decision to eventual champion Lock Haven (Pennsylvania) Little League. Alexandria does not renew its charter, and one year later, the Falls Church Kiwanis Little League is formed as Virginia's first permanently chartered league. |
| 1951 | After two years in which no Virginia leagues enter tournament competition, charters are established in several Virginia communities. Five Virginia leagues (Charlottesville, Danville, Front Royal, and Timberville in Eastern Virginia, and Norton in Western Virginia) joined six West Virginia leagues for the District 4 tournament in Region 4, which spanned New Jersey, Delaware, Maryland, Virginia, and West Virginia. Western Virginia's Norton Little League -- the first integrated league in the South -- defeated Charlottesville Little League, 12-3, to win the Virginia state tournament before falling to Fairmont (West Virginia) Little League 9-0 in the district championship game. |
| 1952 | Little League Baseball's presence in Virginia expands, and the state is organized into three districts. During this era of rapid growth, Little League's tournament structure changed annually, and between 1952 and 1956, Virginia leagues are typically organized into three or four districts. No state tournament is held as Virginia and West Virginia leagues are intermingled in district and sectional tournament competition. |
| 1957 | Little League Baseball reorganizes its tournament structure, and the first annual Virginia state tournament is held. Four district champions from throughout Virginia compete for the right to advance to the Southern Region Division 4 tournament. Although the event determined Virginia's champion, it was held in and won by a league based in Tennessee, as homestanding Bristol Western Little League defeated Hampton Wythe Little League, 7-5, in the championship game of a tournament played on West Cedar Street in Bristol, Tennessee. |
| 1958 | Virginia reorganizes its districts, expanding the total number to six, and establishes the district structure that the state's current organization is derived from. All district champions advance to the state tournament, which will remain a single-elimination event through the 1994 international tournament. |
| 1959 | The Southern Region tournament is held in Virginia as Naval Station Norfolk serves as the host for four teams that compete for a berth in the Little League World Series. The tournament would return to Norfolk each year through 1966, and then again in 1971, before shifting its location to Little League Baseball's new Southern Region headquarters in Gulfport, Florida. |
| 1961 | District 7 (Virginia peninsula) is formed as a split from District 5 (Richmond area), and District 8 (Eastern Shore, Norfolk, and Virginia Beach areas) is formed as a split from District 6 (Coastal Virginia). |
| 1971 | District 4 (Northern Virginia) had grown to encompass 36 leagues, so Virginia officials split this geography into three districts, establishing District 9 (Interstate 95 corridor south of the Washington D.C. Capital beltway) and District 10 (Western Fairfax County, Loudoun County, and surrounding areas). Also in 1971, Virginia's state champion begins advancing directly to the Southern Region tournament rather than first competing in a divisional tournament. With the exception of 1975, Virginia's champion has continued to advance directly to regional tournament competition in every year since this time. |
| 1973 | District 11 (Appalachia Region in Western Virginia) is formed as a split from District 1, and District 12 (Central Virginia - Roanoke and surrounding areas) is formed as a split from District 2. |
| 1989 | District 13 (Lee, Wise, and portions of Dickinson Counties in Western Virginia) is formed as a split from District 11. |
| 1995 | Virginia officials switch the state tournament to a double elimination format. For one year only, Virginia establishes sectional tournaments that feed into the state tournament. The state's 13 districts are organized into four sections, and after double elimination sectional tournament competition, the four winners advance to a double elimination state tournament. Chesterfield American Little League (Midlothian), which is led by future major league pitcher Sean Marshall, defeats Dale City Little League, 7-0, to win the state tournament after emerging from the elimination bracket. |
| 1996 | District 14 (Central Virginia - Charlottesville and environs) is formed as a split from District 2, and District 15 (13 counties adjoining Chesapeake Bay and the tidal portion of the Potomac River) is formed as a split from District 5. Also in 1996, Virginia officials eliminate sectional tournaments, and advance all 15 district champions to a double elimination state tournament. |
| 2001 | Virginia is assigned to the Southeastern Region as Little League Baseball expands the Little League World Series from eight to sixteen teams. |
| 2005 | District 16 (Faquier and Loudoun Counties) is formed as a split from Districts 3 and 10. With the addition of a sixteenth district, Virginia officials switch the state tournament to a pool competition format. Leagues are divided into four pools for round robin competition, and eight teams advance to a single elimination bracket that determines the state champion. In 2005, once-beaten Central Springfield Little League defeats undefeated York County American Little League (Yorktown), 12-8 in 8 innings, in the state championship game. For the next two years, Virginia changed the championship round format to a best 2-of-3 series, before reverting in 2008 to the single game format used today. |
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