The school opened in 1960 in the midst of a population shift toward the south side of Sheboygan and the Town of Wilson.

The most recent expansion in 2016 was privately financed and sponsored by several local companies, including Kohler and Sargento, which saw a new administrative office area constructed by the commons on the south site of the building, and a new metal/auto shop.

In the recent past, the Acuity Gymnasium played host to a private Fifth Harmony concert on March 19, 2014 sponsored by Milwaukee radio station WXSS and won by South High students in a school spirit contest involving clothing donations to Goodwill Industries.

When concerns over the racial implications of the Native American name were broached, a long debate among students, faculty, alumni and the community at large resulted in a change, one of the first in the state of Wisconsin to be settled long before the May 2010 implementation of a state law allowing easier challenges of Native American nicknames (later repealed in 2013), and one of the first computer-designed high school logos in the pre-Internet age of desktop publishing.

One remnant of the former Redmen name still exists in a mosaic profile of an Indian chief on the front facade of the school's auditorium.