This is a compilation of
Annapolis
high school
football
coach history.
| 1965 | 1988 | 24 | Al Laramore | 156-68-2 |
| 1989 | 2002 | 14 | Roy Brown | 103-48-0 |
| 2012 | 2021 | 10 | Nick Good-Malloy | 41-46-0 |
| 2004 | 2011 | 8 | Brian Brown | 38-43-0 |
| 1959 | 1965 | 7 | Neville Leonard | 33-20-4 |
| 1948 | 1956 | 9 | Woody Wetherhold | 32-34-1 |
| 1924 | 1928 | 5 | Willis "Bill" White | 14-14-5 |
| 1907 | 1909 | 3 | A. G. "Garey" Lambert | 13-0-1 |
| 1957 | 1958 | 2 | Bill Best | 9-6-1 |
| 1921 | 1922 | 2 | Andreas Holley | 8-5-1 |
| 1911 | 1914 | 4 | Ivan T. Morton | 8-7-4 |
| 2021 | 2024 | 4 | Dewayne Hunt | 8-13-0 |
| 1899 | 1906 | 8 | Walter L. Brady | 6-1-2 |
| 2003 | 2003 | 1 | Dale Castro | 3-7-0 |
| 1947 | 1947 | 1 | Bruce Rentschler | 2-2-1 |
| 1929 | 1929 | 1 | J. W. McCauley | 2-6-0 |
| 1923 | 1923 | 1 | Byron Leitch | 0-4-2 |
