The Wardens of Sing Sing are appointed by the Commissioner of the Department of Corrections and Community Supervision.
- Elam Lynds (1825–1830)
- Robert Wiltse (1830–1840)
- David L. Seymour (1840–1843)
- William H. Peck (warden) (1843–1845)
- Hiram P. Rowell (1845–1848)
- Chauncey Smith (1848–1849)
- Edward L. Potter (January, 1849)
- Alfred R. Booth (July, 1849)
- Munson J. Lockwood (1850–1855)
- C. A. Batterman (1855–1856)
- William Beardsley (warden) (1856–1862)
- Gaylord B. Hubbell (1862–1864)
- Thomas E. Sutton (1864–1865)
- Stephen H. Johnson (1865–1868)
- David P. Forrest (1868–1869)
- Henry Clay Nelson (1869–1870)
- E. M. Russell (1870–1872)
- Henry C. Nelson (1872–1873)
- Gaylord B. Hubbell (1873–1874)
- James Williamson (warden) (September 1874)
- Alfred Walker (warden) (October 1874)
- George R. Youngs (1876–1877)
- Charles Davis (warden) (February 1877)
- Benjamin S. W. Clark (March 1877)
- Charles Davis (warden) (1877–1880)
- Augustus A. Brush (1880–1891)
- W. R. Brown (1891–1893)
- Charles F. Durston (1893–1894)
- Omar Van Leuven Sage (1894–1899) 
- Addison Johnson (1899–1907)
- Jesse D. Frost (1907–1911)
- John S. Kennedy (1911–1913)
- James Connaughton (warden)* (June 1913) acting warden
- James M. Clancy (1913–1914)
- Thomas McCormick (June 1914)
- George Standish Weed* (October 1914) acting warden
- Thomas Mott Osborne (1914–1915)
- George Washington Kirchwey (1915) 
- Thomas Mott Osborne (July 1916) 
- Calvin Derrick (October 1916)
- William H. Moyer (1916–1919)
- Edward V. Brophy (April 1919)
- Daniel J. Grant* (1919–1920) acting warden
- Lewis Edward Lawes (1920–1941)
- Robert John Kirby (1941–1944)
- William F. Snyder (1944–1950)
- Wilfred Louis Denno (1950–1967) 
- John T. Deegan (1967–1969)
- James L. Casscles (1969–1972)
- Theodore Schubin (1972–1975)
- Joseph Higgins* (July 1975) acting warden
- Harold Butler (warden) (October 1975)
- William G. Gard (1975–1977)
- Walter Fogg* (August 1977) acting warden
- Stephen Dalsheim (1977–1980)
- Wilson E.J. Walters (1980–1983)
- James E. Sullivan (warden) (1983–1988)
- John P. Keane (1988–1997)
- Charles Greiner (1997–2000)
- Brian S. Fischer (2000–2007)
- Luis Marshall (2007-2009)
- Dawson J.W. Brown* (January 2009 - July 2009) acting Superintendent
- Philip Heath (2009-2012)
- Michael Capra (2012–present)
* denotes an acting warden who holds the position until a full-time warden can be appointed
- "NYCHS: Guy Cheli's 'Sing Sing Prison' List of Wardens Page". Correctionhistory.org. Retrieved 2010-09-06.
- "O.V. Sage Warden of Sing Sing; Superintendent Lathrop Promotes His Clerk, Who Has Had Charge Since Durston's Death". New York Times. November 20, 1894. Retrieved 2011-05-05.
Austin Lathrop, Superintendent of State Prisons, to-day appointed Omar V. Sage of Catskill Agent and Warden of Sing Sing Prison. ...
- "Dr. Kirchwey Dies. Criminiologist, 86; Dean of Columbia Law School, 1901-10, Was Warden of Sing Sing in 1915-16. Legal Education Pioneer. Advocate of World Peace Was Director of U. S. Employment Service Here After War". New York Times. March 5, 1942. Retrieved 2011-05-05.
Dean of Columbia Law School, 1901-10, Was Warden of Sing Sing in 1915 ...
- "T. M. Osborne To Be Warden At Sing Sing. Noted Prison Reformer Will Take Office on Dec. 1. Approved by Glynn and Whitman. Big Shake-Up Predicted. Warden-Elect Disapproves of Capital Punishment, but Would Make Executions 'Public Exhibitions". New York Times. November 20, 1914. Retrieved 2011-05-04.
Thomas Mott Osborne of Auburn, N.Y., retired manufacturer, world traveler, lecturer, writer, and prison reformer, has accepted the offer of John B. Riley, State Superintendent of Prisons, of the post of the Warden of Sing Sing Prison. He will take office on Dec. 1, and will relieve ex-Judge George S. Weed, who was temporarily assigned to Sing Sing, when Warden Thomas J. McCormick was ousted on Oct. 30 as the result of the Sullivan scandal. ...
- "Sing Sing Prison Gets New Warden. Denno, 24 Years in State's System, Succeeds Retiring Snyder". New York Times. December 23, 1950. Retrieved 2014-09-02.
Wilfred L. Denno, a veteran of twenty-four years of service in the State prison system, was appointed warden of New York's famed Sing Sing prison today ... Robert E. Murphy, 51, principal keeper at Green Haven Prison, who was appointed warden at Auburn to succeed John Foster ...
- "Sing Sing Warden Retiring on Jan. 12". New York Times. December 24, 1966. Retrieved 2014-09-02.
The warden of Sing Sing prison, Wilfred Louis Denno, will retire Jan. 12 after 40 years of working in the state's prisons, the last 16 years as chief of the tightest ship on the Hudson.