[1] Original members were Walnut, Elk Horn–Kimballton, Anita, Cumberland-Massena, Bridgewater–Fontanelle, Adair–Casey, Orient-Macksburg, and Exira.
In 2004, Earlham, who had joined the conference in the late 1990s, left the league to join the West Central Activities Conference, a league covering similar territory that contains larger 1A and smaller 2A schools.
The school had only recently started its athletic program and the Rolling Hills was its first conference.
In 2007, Paton-Churdan, the smallest school in the West Central Activities Conference, became a member of the Rolling Hills, and in 2009 Glidden-Ralston followed them there.
In 2010, East Greene became the third West Central Activities Conference school to jump to the Rolling Hills in the last 4 years, with both Exira and Elk Horn Kimballton sharing in sports at the starts in 2010.