This league was founded in 2018, as longtime independents Cannelton and Medora wanted to form a conference that would include the isolated small schools.

There was also a conference baseball tournament held that year, since there were enough schools with teams and interest.

Their enrollment and sports programs were growing rapidly, and they didn't want the conference to lose its competitiveness.

Pleasant View Christian School was voted in to the conference in September 2021.

Monroe 2019–2020 2022–2023 2020–2021 2019–2020 (no volleyball tournament held in 2020–2021 season due to pandemic) 2020–2021 2022-2023 (co-champs) 2022–2023 2020–2021 2019–2020 2020–2021