The Southwestern Buckeye League was first started in 1944 with Vandalia Butler, Tipp City, Versailles and Milton Union as the Charter Members. In 1947, West Carrollton and Eaton were added to the League. The SWBL was again expanded in 1950-51 to include Trotwood Madison and Wilmington, but Versailles withdrew. During the 1951-52 school year, the League consisted of Butler, Eaton, Milton Union, Tippecanoe, Trotwood Madison and West Carrollton, while the sports included Football, Boys Basketball, Wrestling, Boys Tennis and Boys Track.
In 1953, Randolph (Northmont) and Oakwood entered the SWBL, making it an eight team League that lasted until 1958 when Brookville and Northridge were voted-in as members. At the close of the 1971-72 school year, Eaton dropped-out and Greenville replaced them for the next year. The next change took place at the beginning of the 1975-76 school year when Bellbrook, Carlisle, Dixie and Valley View replaced Butler, Northmont, Trotwood Madison and West Carrollton. Greenville resigned from the SWBL at the close of the 1981-82 school year and was replace by Eaton. At the close of the 1980-81 school year, Milton Union and Tippecanoe announced their withdrawal from the League after the 1981-82 school year. Middletown Madison joined the SWBL in the 1981-82 and Preble Shawnee joined in 1982-83. Both schools began competition in 1984-85.
Milton Union and Waynesville joined the SWBL in 2001-2002. Also, in 2001-2002, the SWBL became two divisions with Bellbrook, Eaton, Milton Union, Oakwood, Preble Shawnee and Valley View being the Southwestern Division. Brookville Carlisle, Dixie, Madison, Northridge and Waynesville are in the Buckeye Division Franklin and Monroe joined the SWBL in 2004-2005. Both schools began competition in 2006-2007. The Southwestern Division consisted of Bellbrook, Brookville, Eaton, Franklin, Milton Union, Oakwood and Valley View. The Buckeye Division consisted of Carlisle, Dixie, Madison, Monroe, Northridge, Preble Shawnee and Waynesville. Milton Union and Monroe switched Divisions in 2010. Dixie, Milton Union, Northridge and Preble Shawnee rsigned from the SWBL at the end of the 2020-2021 season. The SWBL changed to the East and West Divisions in 2021-2022. The East Division will consist of Bellbrook, Franklin, Monroe, Oakwood and Waynesville. The West Division will consist of Brookville, Carlisle, Eaton, Madison and Valley View.
Golf was added as a League sport in 1960-61, Volleyball, Girls Basketball, Girls Tennis and Girls Track in 1975-76, Softball in 1977-78, Boys Soccer in 1986-87, Girls Soccer in 1995-96 and Boys and Girls Cross Country in 1997-98. Boys and Girls Swimming were added in 2001-2002.