Centreville teams played as exclusively as members of the Class D level Eastern Shore League in the 1937–1941 and 1946 seasons.
[2] The Centerville Colts finished fourth in the 1937 Eastern Shore League regular season with a record of 52–43 under Manager Ed O'Rourke.
Centreville placed second in the regular season standings, 2.0 games behind the Dover Orioles as, Edwin Walls served as the Colts' manager.
[14][15][16][17][1] The Centreville Red Sox again qualified for the playoffs in the 1941 Eastern Shore League, which had reduced to six teams after the Dover Orioles and Pocomoke City Chicks franchises folded.
Centreville ended the Eastern Shore League 1941 regular season with a record of 54–52 and placed fourth in the standings, 11.0 games behind the pennant winning Milford Giants.
Qualifying for the Playoffs under managers Edwin Walls, Lee Wortman and Eddie Popowski, the Milford Giants swept the Red Sox in 3 games.
Despite the championship, the Centreville franchise folded following the 1946 season and were replaced in the 1947 Eastern Shore League by the Rehoboth Beach Pirates.
[6][10][23] Each season, the top four teams in the Eastern Shore League qualified for the postseason, structured as a bracket tournament.