Founded in 1954 by the Optimist Club of Wilmington, 2 leagues covered the city which were the Wilmington Optimist at 18th and Broom St. and and West Wilmington Optimist at 6th and Cleveland Ave. It was the first charted little league in New Castle County. In 1957, Kingswood Baseball League was formed to cover the northeast neighborhoods.One of the 3 leagues won DE State Championships in 1958, 1959, 1961, 1962, and were state finalists in 1960, 1965, 1969.

Kingswood merged with Wilmington Optimist in 2000 and in 2002 West Wilmington merged with Wilmington Optimist to create a unified Wilmington Little League. This directly impacted all Wilmington city limit zip codes and approximately 350 players at the time. With Covid in 2020, enrollment dropped but has since bounced back in recent years.