Sheriff's History

1890 Cleveland County Sheriff
1890 - 1893
Sheriff Woody Lyttle
1893 Cleveland County Sheriff
1893 - 1895
1901 - 1903
Sheriff George Smith
1895 Cleveland County Sheriff
1895 - 1897
1898 - 1901
Sheriff H. F. Newblock
1897 Cleveland County Sheriff
1897- 1898
Sheriff Hiram Downing
1903 Cleveland County Sheriff
1903 - 1905
Sheriff L. P. Barker
1905 Cleveland County Sheriff
1905 - 1907
Sheriff R. S. Bryant
1907 Cleveland County Sheriff
1907 - 1913
Sheriff I. B. Sale
1913 Cleveland County Sheriff
1913 - 1917
Sheriff Claud Pickard
1917 Cleveland County Sheriff
1917 - 1919
Sheriff Ben Wheelis
1919 Cleveland County Sheriff
1919 - 1923
Sheriff W. H. Newblock
1923 Cleveland County Sheriff
1923 - 1931
Sheriff Frank Boggs
1931 Cleveland County Sheriff
1931 - 1935
Sheriff W. W. Jennings
 1935 Cleveland County Sheriff
1935 - 1943
Sheriff Irvan Kennedy
 1943 Cleveland County Sheriff
1943 - 1947
Sheriff Key Durkee
 1947 Cleveland County Sheriff
1947 - 1952
Sheriff Jess Jack
 1952 Cleveland County Sheriff
1952 - 1953
Interim Sheriff Mrs. Jack
 1953 Cleveland County Sheriff
1953 - 1963
Sheriff Olen Garner
 1963 Cleveland County Sheriff
1963 - 1984 
Sheriff C. W. Bill Porter
 1984 Cleveland County Sheriff
1984 - 1987
Sheriff Thomas G Kennedy
 1987 Cleveland County Sheriff
1987 - 1992
Sheriff John J Walsh
 1993beggs
1993 - April 2008
Sheriff F. DeWayne Beggs
 2008 Cleveland County Sheriff
May 2008 - Dec. 2008
Interim Sheriff
Don P. Holyfield
JLester
 2009 Cleveland County Sheriff
Jan. 2009 - October 2017 
Sheriff Joseph K. Lester