In 1985, the Rockingham County school board decided to built two new elementary schools in the Bridgewater-Dayton area and to expand the John Wayland Middle School and Turner Ashby High School. However, there was strong sentiment in the area for a new high school and, in 1986, the board, which included two new members from the Bridgewater-Dayton area, abandoned plans for the elementary schools and voted to build a new Turner Ashby High School, convert the old high school to a middle school and convert the old middle school to an elementary school. The plan would close the old elementary schools at Bridgewater and Dayton.

By the fall of 1989, the new Turner Ashby High School opened and the old high school was converted to a middle school and named Wilbur S. Pence Middle School. The school was named after long-time superintendent Wilbur S. Pence (1950-1971) who had lived a short distance from the school. Brownie Cummins, a long-time coach and athletic director at Harrisonburg High School, was named as the first principal at the converted middle school. In 1992, Brownie Cummins left Wilbur S. Pence to become principal at Spotswood High School. He was succeeded by Jo Anne Wenger, who had been a former principal in the county (Bergton-1972-74) and had taught math at John C. Myers Middle School. She resumed her administrative career in Shenandoah county and returned to Rockingham County in 1991 as a central office elementary supervisor. Mrs. Wenger served the school until 1997, when she became principal at Linville-Edom Elementary school. James Slye, who had been a central office supervisor, was named the new principal at Wilbur S. Pence Middle School. He served as principal until 1999 when he was named as the principal of Spotswood High School. Mary Shifflett was named principal and still serves in that position.

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