Clover Hill and Lunenburg-Central became district members a few years later. The James River District was reorganized in 1999 with seven charter members, Central High School (also known as Lunenburg or Lunenburg Central), Prince Edward County High School, Buckingham High School, Amelia County High School, Randolph-Henry High School, and Cumberland High School. After the 1999 season, Prince Edward moved to a different district.
Later on, Clover Hill and Lunenburg-Central became part of the district. The James River District underwent restructuring in 1999 with seven original members including Central High School (also known as Lunenburg or Lunenburg Central), Prince Edward County High School, Buckingham High School, Amelia County High School, Randolph-Henry High School, and Cumberland High School. After the 1999 season, Prince Edward County switched to a different district.