The mall opened in 1988, with anchor stores Dillard's and Sears, in what was a remote location surrounded mostly by farmland. As a result of a less than ideal location and the stagnant Texas economy in the late eighties, the mall initially struggled. A 6-screen movie theater operated by Santikos Theatres (and then turned over to Regal Cinemas) opened within a few years. (It eventually became a dollar cinema before closing in 2001. An Inflatable Wonderland is now open in its place.)
As the city grew to meet the mall, Rolling Oaks has repositioned itself and is a stable retail center. In 1992 the mall expanded its retail area with a new wing and added a third anchor, Foley's (now Macy's). Additionally, J.C. Penney opened a new store at the mall in 2004. There is one additional location designated for a future anchor included in the master plan of the mall that is currently used as a parking lot.