Principals at San Dieguito
| Principals | Years |
| Arthur M. Main | 1936-1939 |
| Donovan Cartwright | 1940-1945 |
| Tom Preece | 1946-1949 |
| William Mace | 1950-1951 |
| Matthew Korwin | 1952-1959 |
| Donald Crickmore | 1960 |
| John Clark | 1961-1968 |
| Leonard Morris | 1969-1976 |
| William Hershey | 1977-1981 |
| Salvador Ramirez | July 1981 through June 19931 |
| Penny Cooper-Francisco | 1994-1995 |
| Don Rizzi | 1996 |
| Fran Fenical | 1997-2002 |
| Don Rizzi | Fall 2002 through Spring 2005 |
| Barbara Gauthier | Fall 2005 through June 2008 |
| Michael Grove | July 2008 to present |
SOURCES: San Dieguito High School Academy yearbooks, except where noted below.
1Mr. Salvador Ramirez