This is a compilation of
Holliston
high school
football
coach history.
| 2003 | 2023 | 21 | Todd Kiley | 173-59-0 |
| 1968 | 1975 | 8 | Tom Caito | 56-16-3 |
| 1983 | 1989 | 7 | Bob Bradford | 52-20-0 |
| 1993 | 2002 | 10 | Ed Buckley | 29-74-0 |
| 1990 | 1992 | 3 | Jim Reilly | 26-5-0 |
| 1957 | 1961 | 5 | Angelo Insalaco | 21-12-2 |
| 1976 | 1979 | 4 | Paul Rowles | 20-16-3 |
| 1980 | 1982 | 3 | Bill McKeown | 19-12-0 |
| 1964 | 1967 | 4 | Vincent Messina | 15-18-3 |
| 1900 | 1903 | 4 | Fred Holland Wilson Cutler | 14-7-0 |
| 1924 | 1925 | 2 | Peter Newell | 9-7-0 |
| 1962 | 1963 | 2 | Nelson Bebo | 7-6-2 |
| 2024 | 2024 | 1 | Michael Yuroff | 5-6-0 |
| 1920 | 1923 | 4 | unknown | 2-4-0 |
| 1897 | 1899 | 3 | James L. Leary | 2-6-1 |
| 1909 | 1909 | 1 | Edwin Bradley Richards | 1-2-1 |
| 1896 | 1896 | 1 | Fred Clay Tenney | 1-4-2 |
| 1905 | 1905 | 1 | Thomas L. Griffin | 0-2-1 |
