======  Chesapeake All-Time Football Results ======

^ Year      ^ Record       ^ Coach          ^ Extra Info ^
| 1926 | 0-4 |
| 1927 | 1-3 |Dana Lough|
| 1928 | 1-2 |Dana Lough|
| 1929 | 2-4-3 |Doss Richardson|
| 1930 | 2-4 |Didge Hensley|
| 1931 | 6-4-1 |Dana Lough|
| 1932 | 5-3-2 |Dana Lough|
| 1933 | 4-1-2 |Phoney Smith|
| 1934 | 4-4-1 |Phoney Smith|
| 1935 | 2-6-1 |Emerson "Tip" Wood|
| 1936 | 2-5-1 |Emerson "Tip" Wood|
| 1937 | 3-4 |Emerson "Tip" Wood|
| 1938 | 4-4 |Herndon Wilkes|
| 1939 | 3-5-3 |Herndon Wilkes|
| 1940 | 5-3-1 |Herndon Wilkes|
| 1941 | 4-6 |Paul Hogan|
| 1944 | 2-3 |Merrill Payne - Dick DeLong|
| 1945 | 2-6 |
| 1946 | 4-7 |Tom Hesson|
| 1947 | 7-3 |Tom Hesson|
| 1948 | 6-2-2 |Tom Hesson|
| 1949 | 3-7-1 |Tom Hesson|
| 1950 | 8-2-1 |Tom Hesson|
| 1951 | 3-7 |Dave Smith|
| 1952 | 2-8 |Dave Smith|
| 1953 | 2-8 |Dave Smith|
| 1954 | 4-6 |Dave Smith|
| 1955 | 3-7 |Dave Smith|
| 1956 | 4-5-1 |Dan Russell|
| 1957 | 3-7 |Chuck Barton|
| 1958 | 1-9 |Gil Smith|
| 1959 | 6-3-1 |Gil Smith|
| 1960 | 6-2-1 |Jim Conard|
| 1961 |10-0 |
| 1962 | 3-6 |Carl Little|
| 1963 | 5-4 |Ralph May|
| 1964 | 5-4 |Ralph May|
| 1965 | 7-3 |Ralph May|
| 1966 | 2-8 |Don Futton|
| 1967 | 4-6 |Bernie Staley|
| 1968 | 3-7 |Bernie Staley|
| 1969 | 3-7 |Ben Coleman|
| 1970 | 2-6-1 |Ben Coleman|
| 1971 | 3-6 |Ben Coleman|
| 1972 | 4-4-1|Ben Coleman|
| 1973 | 4-6 |Ben Coleman|
| 1974 | 5-5 |Ben Coleman|
| 1975 | 8-2 |Ben Coleman|
| 1976 | 6-3-1 |Ben Coleman|
| 1977 | 3-5-2|Ben Coleman|
| 1978 | 8-1-1|Ben Coleman|
| 1979 | 5-5 |Ben Coleman|
| 1980 | 4-6 |Ben Coleman|
| 1981 | 3-7 |Ben Coleman|
| 1982 | 2-7 |Steve Lambert|
| 1983 | 6-4 |Steve Lambert|
| 1984 | 9-1 |Steve Lambert|
| 1985 | 2-8 |Steve Lambert|
| 1986 | 5-5 |Les DeLong|
| 1987 | 4-6 |Les DeLong|
| 1988 | 0-10|Les DeLong|
| 1989 | 1-9 | Phil Davis |  |
| 1990 | 3-7 | Phil Davis |  |
| 1991 | 6-4 | Phil Davis |  |
| 1992 | 3-7 | Phil Davis |  |
| 1993 | 4-6 | Phil Davis |  |
| 1994 | 6-4 | Phil Davis |  |
| 1995 | 2-8 | Phil Davis |  |
| 1996 | 8-3 | Phil Davis | Playoffs |
| 1997 | 8-2 | Phil Davis |  |
| 1998 | 8-3 | Phil Davis | Playoffs |
| 1999 | 11-1 | Phil Davis | Playoffs |
| 2000 | 8-2 | Phil Davis |  |
| 2001 | 7-4 | Phil Davis | Playoffs |
| 2002 | 9-4 | Phil Davis | Regional Runner-up |
| 2003 | 8-3 | Phil Davis | Playoffs |
| 2004 | 8-3 | Phil Davis | Playoffs |
| 2005 | 6-4 | Phil Davis |  |
| 2006 | 4-6 | Phil Davis |  |
| 2007 | 3-7 | Phil Davis |  |
| 2008 | 4-6 | Phil Davis |  |
| 2009 | 4-6 | Phil Davis |  |
| 2010 | 5-5 | Phil Davis |  |
| 2011 | 7-4 | Andy Clark | Playoffs |
| 2012 | 5-5 | Andy Clark |  |
| 2013 | 2-8 | Andy Clark |  |
| 2014 | 6-4 | Andy Clark |  |
| 2015 | 8-3 | Andy Clark | Playoffs |
| 2016 | 9-2 | Andy Clark | Playoffs |
| 2017 | 4-6 | Andy Clark |  |
| 2018 | 5-5 | Andy Clark |  |
| 2019 | 4-6 | Todd Knipp |  |
| 2020 | 2-5 | Todd Knipp | Playoffs |
| 2021 | 0-8 | Todd Knipp |  |
| 2022 | 2-8 | Todd Knipp |  |
| 2023 | 3-7 | Todd Knipp |  |
| 2024 | 5-6 | Todd Knipp | Playoffs |