This is a compilation of
Windsor Academy
high school
football
coach history.
| 2019 | 2022 | 4 | Randy Grace | 40-8-0 |
| 2006 | 2010 | 5 | Mike Smallwood | 31-26-0 |
| 1974 | 1979 | 6 | John Abbott | 30-20-2 |
| 2012 | 2016 | 5 | Jimmy Watts | 21-32-0 |
| 1994 | 1999 | 6 | Ricky Ellis | 19-45-0 |
| 1990 | 1993 | 4 | Gayle Reeves | 18-22-2 |
| 1980 | 1980 | 1 | Jimmy Hammond | 11-1-0 |
| 1984 | 1986 | 3 | Bill Peake | 9-23-1 |
| 1987 | 1988 | 2 | Al Pollard | 8-12-0 |
| 2002 | 2004 | 3 | Jeff Benefield | 8-27-1 |
| 2000 | 2001 | 2 | Don Marchman | 6-17-0 |
| 2018 | 2018 | 1 | Matt Britt | 4-5-0 |
| 2011 | 2012 | 2 | Ricky Worsham | 4-10-0 |
| 1982 | 1983 | 2 | Durwood Sauls | 3-17-0 |
| 2005 | 2005 | 1 | Gayle Reeves | 2-10-0 |
| 1991 | 1991 | 1 | Bobby Bedgood | 1-9-0 |
| 1981 | 1981 | 1 | Hershel Wynn | 1-9-0 |
| 2017 | 2017 | 1 | Bill Beaty | 0-10-0 |
