 
 This is a list of the Masters (later Headmasters) and Ushers (later Second Masters) of Gresham's School, Holt.
Thomas Beckwith used the title "undermaster" in 1821. [12]
The Junior School was reorganized into the Preparatory School and the Pre-Preparatory School in 1984.
| House | Housemaster | Assistant housemaster | 
|---|---|---|
| Howson's | J. Cowan | E. Robinson | 
| Farfield | T. Burnett | J. Beales | 
| Tallis | C. Cox | C. Oates | 
| Woodlands | J. Sharrock | S. Knightbridge | 
| House | Housemistress | Assistant Housemistress | 
|---|---|---|
| Edinburgh | E. Fern | E. Wilson | 
| Queens' (formerly Britten) | V. Seldon | E. Philpott | 
| Oakeley | O. Ravilious | D. Majid |