Headmasters Since 1558
- William Bradshawe (1558–1600)
- Thomas Taylor (1600–1606)
- Richard Ward (1606–1647)
- William Holmes (1647–1664)
- Dr. Robert Uvedale (1664–1676)
- William Nelson (1678–1700)
- Thomas Harper (1700–1721)
- The Revd. John Davis (1721–1732)
- The Revd. John Allen (1732–1761)
- The Revd. Daniel Shipton (1761–1762)
- The Revd. Samuel Hardy (1762–1791)
- The Revd. John Milne (1791–1831).
- James Emery (1831–1846).
- Charles Chambers (1847–1874).
- J Jackson (1875). .
- W.G. MacDonald. (1876–1877).
- W. S. Ridewood (1877–1909).
- E. M. Eagles (1909–1934).
- L.C. Soar (1934-1964)
- Dr. L. Whitworth (1964-1980)
- Malcolm McAlpine (1980-1987)
- David Thomas (1987-1995)
- David Daniels (1995-2001)
- Michael C. Weeks (2001-2006)
- John Kerr (2006 – present)
See: J.S. Cockburn, H.P.F. King, K.G.T. McDonnell (Editors. A History of the County of Middlesex: Volume 1; 1969. Also: Google scholar.
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