The Dairyland Conference was formed by six small high schools in west central Wisconsin in 1959.
[9] In 1989, Blair and Taylor merged to form Blair-Taylor High School, inheriting both predecessors' Dairyland membership in the process.
The Pepin/Alma cooperative inherited Alma's place in the Dairyland Conference's Small Schools division.
[25] Two years later, Independence and Gilmanton became a cooperative program and remained in the Small Schools division.
Cochrane-Fountain City moved over to the Small Schools division to balance the alignment at five schools per division:[26] In 2025, Osseo-Fairchild will make its return to the Dairyland Conference after nearly four decades of Cloverbelt Conference membership.