List of headmasters of St. Bees School
The list of headmasters of St. Bees School includes the men and one woman who have held the headmastership of St. Bees School in west Cumbria. Under the statutes drawn up by the school's founder, Archbishop Edmund Grindal, the headmaster of the school was chosen by the Provost of the Queen's College, Oxford. This state of affairs lasted until 1879 when a "new scheme" came into place and the board of governors had a greater say in the appointment.
In the early days of the school the headmaster was the sole master, his school being a one-story stone building. In the nineteenth century, St. Bees School began to expand thanks to the proceeds from mineral royalties, legally won in part by the efforts of Headmaster William Wilson, and in 1844 the headmaster moved into the newly built south wing of the "Quad", the quadrangle of sandstone buildings which makes up the main and oldest part of the school. In 1886, a purpose built home was constructed called the "School House", part of which today serves as a senior boys' boarding house.
List of headmasters at St. Bees School
| Years | Name | Alma mater | References |
| 1583–1593 | Nicholas Copland, B.A. | - | |
| 1593–1612 | William Briscoe, M.A. | - | |
| 1612–1630 | William Lickbarrow, M.A. | - | |
| 1630–1679 | Francis Radcliffe, M.A. | The Queen's College, Oxford | |
| 1679–1681 | Bernard Gilpin, B.A. | The Queen's College, Oxford | |
| 1681–1686 | Jonathan Banks, B.A. | Pembroke College, Cambridge | |
| 1686–1738 | Rev. Richard Jackson, M.A. | The Queen's College, Oxford | |
| 1738–1755 | Rev. Alan Fisher, B.A. | The Queen's College, Oxford | |
| 1755–1773 | Rev. John James, M.A. | The Queen's College, Oxford | |
| 1773–1788 | Rev. Robert Scott, M.A. | The Queen's College, Oxford | |
| 1788–1791 | Rev. James Hutchinson, M.A. | The Queen's College, Oxford | |
| 1791–1811 | Rev. John Barnes, M.A. | The Queen's College, Oxford | |
| 1811–1817 | Rev. William Wilson, M.A. | The Queen's College, Oxford | |
| 1817–1830 | Rev. Thomas Bradley, M.A. | The Queen's College, Oxford | |
| 1830–1841 | Rev. John Fox, M.A. | The Queen's College, Oxford | |
| 1841–1854 | Rev. Miles Atkinson, M.A. | The Queen's College, Oxford | |
| 1854–1879 | Rev. George Henry Heslop, M.A. | The Queen's College, Oxford | |
| 1879–1903 | Rev. William Taylor Newbold, M.A. | St John's College, Cambridge | |
| 1903–1916 | Rev. Harold Athelstane Parry Sawyer, M.A. | The Queen's College, Oxford | |
| 1917–1926 | Cecil William Kaye, M.A. | University College, Oxford | |
| 1926–1935 | Edward Allen Bell, M.A. | Christ Church, Oxford | |
| 1935 | Robert Branston Brown, M.A. | Trinity Hall, Cambridge | |
| 1936–1938 | Howard George Charles Mallaby, M.A. | Merton College, Oxford | |
| 1938–1945 | Rev. John Sidney Boulter, M.B.E., T.D., M.A. | Keble College, Oxford | |
| 1945–1946 | C.G.S. Harden, M.A. | St. John's College, Cambridge | |
| 1946–1951 | Henry Enfield Reekie | Clare College, Cambridge | |
| 1951–1963 | James Cochrane Wykes, M.A. | Clare College, Cambridge | |
| 1963–1980 | Geoffrey William Lees, M.A. | Downing College, Cambridge | |
| 1980–1988 | Malcolm Tod Thyne, M.A. | Clare College, Cambridge | |
| 1988–1997 | Paul Arthur Chamberlain, B.Sc. | University of Durham | |
| 1997 | Philip James Etchells, B.Sc., Ph.D. | University of Liverpool | - |
| 1998–2000 | Janet Dolton Pickering, B.Sc. | University of Sheffield | |
| 2000–2012 | Philip J. Capes, M.A. | University of Exeter | |
| 2012–2015 | James Davies | University of Sheffield |