15th century

• Henry Sever (1440–1442)
• William Waynflete (1442–1447)
• John Clerk (1447)
• William Westbury (1447–1477)
  Thomas Barker (1447) ^[a]

16th century

• Henry Bost (1477–1504)
• Roger Lupton (1504–1535)
• Roger Aldrich (1535–1547)
• Sir Thomas Smith (1547–1554)
• Henry Cole (1554–1559)
• William Bill (1559–1561)
  Richard Bruerne (1561) ^[b]
• William Day (1561–1596)

17th century

• Sir Henry Savile (1596–1622)
• Sir Thomas Murray (1622–1623)
• Sir Henry Wotton (1624–1639)
• Richard Steward (1639–1644)
• Francis Rous (1644–1659)
• Nicholas Lockyer (1659–1660)
• Nicholas Monck (1660–1661)
• John Meredith (1662–1665)
• Richard Allestree (1665–1680)
• Zachary Cradock (1681–1695)

18th century

• Henry Godolphin (1695–1732)
• Henry Bland (1733–1746) previously Head Master 1720–1728
• Stephen Sleech (1746–1765)
• Edward Barnard (1765–1781) previously Head Master 1754–1765
• William Hayward Roberts (1781–1791)

19th century

• Jonathan Davies (1791–1809) previously Head Master 1773–1792
• Joseph Goodall (1809–1840) previously Head Master 1802–1809
  John Lonsdale (1840) ^[a]
• Francis Hodgson (1840–1853)
• Edward Craven Hawtrey (1853–1862) previously Head Master 1834–1853
• Charles Old Goodford (1862–1884) previously Head Master 1853–1862

20th century

• James John Hornby (1884–1909) previously Head Master 1868–1884
• Edmond Warre (1909–1918) previously Head Master 1884–1905
• Montague Rhodes James (1918–1936)
• Hugh Cecil, 1st Baron Quickswood (1936–1944) ^[c]
• Sir Henry Marten (1945–1949)
• Sir Claude Aurelius Elliott (1949–1965) previously Head Master 1933–1949
• Harold Caccia, Baron Caccia (1965–1978)
• Martin Charteris, Baron Charteris of Amisfield (1978–1991)
• Sir Antony Acland (1991–2000)

21st century

• Sir Eric Anderson (2000–2009) previously Head Master 1980–1994
• William Waldegrave, Baron Waldegrave of North Hill (2009–2024)
• Sir Nicholas Coleridge (2024–present) ^{[1] [2] [3]}

Notes