Former pupils of Winchester made a significant impact on the archaeology of the Mediterranean world in the period prior to the First World War. Three of the first four directors were educated there:
- Penrose, Francis Cranmer (1817–1903), director 1886-87
- Smith, Cecil Harcourt [later Sir Cecil Harcourt-Smith] (1859-1944), director 1895-97
- Hogarth, David George (1862-1927), director 1897-1900
- Herbert Awdry (1851-1909)
- John Frederick Randall Stainer (1866-1939), son of Sir John Stainer
- (Sir) John Linton Myres (1869-1954)
- Guy Dickins (1881-1916)
- Alexander Craddock Bolney Brown (1882-1942)
- George Leonard Cheesman (1884-1915)
- William Reginald Halliday (Hoffmeister) (1886-1966)
- Cyril Bertram Moss-Blundell (c. 1890-1915)
Rev. Alfred Hamilton Cruikshank (1862-1927), an exact contemporary of Hogarth at Winchester, was an associate student of the BSA. He returned to Winchester (from Harrow) as an assistant master in 1894 (and chaplain from 1896); he left for Durham in 1910.
Other Wykehamist archaeologists of this era included Arthur Hamilton Smith (1860-1941), Keeper at the British Museum and later director of the British School at Rome; Francis John Haverfield (1860–1919), Camden professor of ancient history at Oxford; and Thomas Ashby (1874–1931), director of the British School at Rome.