Osceola Kowboys
est 1887

1950 5-5 HC Bill Stephens
1951 5-3 HC Bill Stephens
1952 7-2 HC Bill Stephens
1953 6-4 HC Bill Stephens
1954 5-4-1 HC Bill Stephens
1955 6-3 HC Bill Stephens
1956 3-7 HC Bill Stephens
1957 2-8 HC Bill Stephens
1958 0-10 HC Casey Stephenson
1959 4-6 HC Jack Yearwood
1960 6-4 HC Jack Yearwood
1961 10-1 HC Jack Yearwood (Ridge Conf. Championship loss v Sebring)
1962 6-2-2 HC Jack Yearwood
1963 8-3 HC Jack Yearwood (Frontier Bowl loss v Sanford)
1964 8-3 HC Jack Yearwood (Tangelo Bowl win v Eustis)
1965 7-3 HC Jack Yearwood
1966 4-6 HC Dewayne Douglas
1967 6-4 HC Dewayne Douglas
1968 2-8 HC Donald Daniels
1969 2-8 HC Bill Duty
1970 7-4 HC Bill Duty (Kowboy Classic Bowl loss v Eau Gallie)
1971 4-5-1 HC Richard Hagy
1972 2-8 HC Richard Hagy
1973 6-5 HC Richard Hagy (Citrus Bowl loss v Hernando)
1974 3-7 HC Larry Bottom
1975 3-7 HC Jim Yancey
1976 3-7 HC Jim Yancey
1977 5-5 HC Jim Scible
1978 4-6 HC Jim Scible
1979 8-3 HC Jim Scible (Elks Bowl loss v Colonial)
1980 7-3 HC Jim Scible
1981 7-4 HC Ken Baker (Rotary Bowl loss v Winter Park)
1982 11-3 HC Ken Baker District Champions,Regional Champions,State Runner-Up
1983 8-3 HC Ken Baker (Citrus Bowl win v Crystal River)
1984 6-5 HC Ken Baker (Elks Bowl loss v Apopka)
1985 6-4 HC Ken Baker
1986 2-8 HC Mike Vogt
1987 9-1 HC Mike Vogt
1988 4-6 HC Greg Johnson
1989 6-5 HC Greg Johnson (Scholarship Bowl loss v Rickards)
1990 10-3 HC Greg Johnson District Champions,Regional Champions
1991 6-5 HC Greg Johnson (Scholarship Bowl loss v West Orange)
1992 4-6 HC Greg Johnson
1993 5-5 (4-6) HC Greg Johnson (forfeit win v Winter Haven)
1994 5-5 HC Greg Johnson
1995 1-9 (6-4) HC Greg Johnson (5 wins forfeited)
1996 7-3 HC Jim Scible
1997 11-2 HC Jim Scible District Runner-Up,Regional Champions
1998 13-2 HC Jim Scible District Champions,Regional Champions,State Champions
1999 13-1 HC Jim Scible District Champions,Regional Champions
2000 10-3 HC Jim Scible District Champions
2001 12-1 HC Jim Scible District Champions
2002 6-5 HC Jim Scible District Runner-Up
2003 8-4 HC Jim Scible District Runner-Up
2004 3-6 HC Jim Scible
2005 2-8 HC Jim Scible
2006 8-3 HC Jeff Rolson (Rotary Bowl win v Harmony)
2007 14-1 HC Jeff Rolson District Champions,Regional Champions,State Runner-Up
2008 8-4 HC Jeff Rolson District Runner-Up
2009 7-5 HC Jeff Rolson District Runner-Up
2010 5-6 HC Doug Nichols District Runner-Up
2011 10-2 HC Doug Nichols District Champions
2012 13-1 HC Doug Nichols District Champions,Regional Champions
2013 11-3 HC Doug Nichols District Champions,Regional Champions
2014 13-2 HC Doug Nichols District Champions,Regional Champions,State Runner-Up
2015 13-2 HC Doug Nichols District Champions,Regional Champions,State Runner-Up
2016 10-1 HC Doug Nichols District Champions
2017 10-1 HC Doug Nichols District Champions 1 seed
2018 9-2 HC Doug Nichols District Champions 2 seed
2019 10-2  HC Doug Nichols District Champions 3 seed
2020