List of Phillips Academy Heads of School
This is a complete list of the Principals of Phillips Academy since its founding in 1778. From 1778 to 1928, the title was "Principal". In the year 1928, the name was changed to "Headmaster", and finally with the appointment of Barbara Landis Chase, the title was again changed to "Head of School".
| Image | Head of School | Accessus | Exitus | |
| 1 | Eliphalet Pearson, LL.D. | 1778 | 1786 | |
| 2 | Ebenezer Pemberton, A.M. | 1786 | 1793 | |
| 3 | Mark Newman, A.M. | 1795 | 1809 | |
| 4 | John Adams, A.M., LL.D. | 1810 | 1833 | |
| 5 | Osgood Johnson, A.M. | 1833 | 1837 | |
| 6 | Samuel Harvey Taylor, LL.D. | 1837 | 1871 | |
| 7 | Frederic W. Tilton, A.M. | 1871 | 1873 | |
| 8 | Cecil Bancroft, PH.D., L.H.D., LL.D. | 1873 | 1901 | |
| 9 | Alfred Stearns, LITT.D., L.H.D., LL.D. | 1903 | 1933 | |
| 10 | Claude Fuess, PH.D., LITT.D., L.H.D., LL.D. | 1933 | 1948 | |
| 11 | John M. Kemper, L.H.D., LITT.D., LL.D. | 1948 | 1971 | |
| 12 | Theodore Sizer, PH.D., PED.D., LITT.D. | 1972 | 1981 | |
| 13 | Donald McNemar | 1981 | 1994 | |
| 14 | Barbara Landis Chase | 1994 | 2012 | |
| 15 | John Palfrey | 2012 | 2019 | |
| 16 | Raynard S. Kington | 2020 | current |