Boys basketball district champions

Casey Lester played in three state tournaments with Harlan in the 1990s.

2023 xxxx
2022 Bell County 88, Harlan 78 (2 OT)
2021 Harlan 61, Harlan County 55
2020 Harlan County 58, Harlan 54
2019 Middlesboro 58, Harlan 55
2018 Harlan County 46, Harlan 43
2017 Harlan County 68, Harlan 50
2016 Harlan County 68, Bell County 43
2015 Harlan County 53, Bell County 40
2014 Bell County 76, Middlesboro 50
2013 Harlan County 83, Middlesboro 57
2012 Middlesboro 53, Harlan County 48
2011 Bell County 62, Harlan County 53
2010 Harlan County 78, Bell County 73
2009 Middlesboro 77, Harlan County 65
2008 Bell County 58, Cumberland 56
2007 Bell County 51, Cumberland 49
2006 Bell County 48, Cawood 43
2005 Cawood 57, Harlan 45
2004 Cawood 61, Cumberland 54
2003 Cumberland 78, Evarts 62
2002 Cawood 95, Evarts 73
2001 Cawood 99, Evarts 69
2000 Harlan 69, Cawood 68
1999 Harlan 67, Cawood 52
1998 Cawood 70, Harlan 57
1997 Harlan 71, Evarts 54
1996 Harlan 72, Evarts 54
1995 Harlan 68, Evarts 60
1994 Harlan 72, Cawood 60
1993 Cumberland 78, Harlan 74
1992 Cawood 79, Evarts 57
1991 Cawood 71, Cumberland 69
1990 Harlan 80, Cawood 78
1989 Cumberland 56, Harlan 47
1988 Evarts 48, Cumberland 45
1987 Harlan 60, Cawood 52
1986 Cawood 67, Harlan 60
1985 Cumberland 78, Harlan 54
1984 Cumberland 58, Cawood 55
1983 Evarts 71, Cawood 68
1982 Cawood 70, Cumberland 69
1981 Cawood 87, Lynch 67
1980 Lynch 61, Harlan 41
1979 Harlan 55, Cumberland 50
1978 Cawood 63, Cumberland 58
1977 Cawood 72, Cumberland 66
1976 Cawood 72, Evarts 59
1975 Lynch 68, Cumberland 52
1974 Lynch 67, Harlan 61
1973 Cumberland 48, Harlan 47
1972 Cumberland 52, Lynch 42
1971 Cumberland 60, Lynch 54
1970 Cumberland 46, Evarts 34
1969 Harlan 61, Evarts 33
1968 Harlan 88, Cumberland 51
1967 Harlan 73, Lynch 67
1966 Lynch 68, Harlan 51
1965 Harlan 64, Lynch 60
1964 Lynch 62, Harlan 57
1963 Evarts 41, Cumberland 39
1962 Rosenwald 61, Cumberland 50
1961 Loyall 58, Harlan 37
1960 Black Star 54, Cumberland 53
1959 Harlan 69, Benham 52
1958 Rosenwald 60, Hall 56
1957 Hall 74, Cumberland 69
1956 Black Star 69, Loyall 62
1955 Cumberland 53, Hall 36
1954 Harlan 68, Wallins 65
1953 Wallins 47, Harlan 43
1952 Loyall 52, Wallins 46
1951 Harlan 60, Lynch 53
1950 Hall 70, Cumberland 64
1949 Hall 57, Benham 47
1948 Hall 48, Harlan 29
1947 Benham 51, Hall 42
1946 Hall 38, Benham 36
1945 Harlan 51, Hall 20
1944 Harlan 58, Loyall 37
1943 Harlan 29, Hall 16
1942 Harlan 49, Lynch 33
1941 Black Star 23, Benham 21 (2OTs)
1940 Benham 39, Harlan 27
1939 Benham 44, Cumberland 16
1938 Loyall 24, Harlan 22
1937 Benham 25, Black Star 17