School superintendents that have served Princess Anne County and Virginia Beach are:
- Edgar B. Macon, 1870 - 1880
- A.B. Malbone, 1880 - 1885
- O. B. Mears, 1885 - March 1921
- J.H. Carroll, March 1921 - June 1929
- Robert Johnson, July 1929 - June 1933
- Frank W. Cox*, July 1933 - February 1968
- Edward E. Brickell, March 1968 - June 1987
- James E. Melvin, July 1987 - September 1989
- E. Carlton Bowyer, September 1989 - November 1990
- K. Edwin Brown, Acting - December 1990
- S. John Davis, Interim - January 1991 - June 1991
- Sidney L. Faucette, July 1991 - June 1995
- James L. Pughsley, Interim - June 1995 - February 1996
- Timothy R. Jenney, February 1996 - June 2005
- Sheila S. Magula, June 2005 - June 2006
- James G. Merrill, July 2006 - June 2013
- Sheila S. Magula, June 2013 - June 2014
- Aaron C. Spence, June 2014 - present
In an 1847 referendum, Princess Anne County voters committed themselves to a tax-supported public school system. In 1870, the Virginia Constitution provided that all localities must establish public school systems, presided over by a superintendent. (Princess Anne County/Virginia Beach Historical Society)
*January 1, 1963 - City of Virginia Beach formed as a result of a merger with Princess Anne County.