Chicago Film Critics Association Award for Best Supporting Actor

Winners
Names and titles in bold indicate actors that won the Academy Award for Best Supporting Actor. Names and titles with an asterisk (*) indicate films that were nominated for the Academy Award for Best Supporting Actor, but did not win.
 * 1988 - Martin Landau*, Tucker: The Man and His Dream
 * 1989 - Danny Aiello*, Do the Right Thing
 * 1990 - Joe Pesci, Goodfellas
 * 1991 - Harvey Keitel*, Bugsy
 * 1992 - Jack Nicholson*, A Few Good Men
 * 1993 - Ralph Fiennes*, Schindler's List
 * '1994' - Martin Landau, Ed Wood
 * '1995' - Kevin Spacey, The Usual Suspects
 * '1996' - Cuba Gooding Jr., Jerry Maguire
 * 1997 - Burt Reynolds*, Boogie Nights
 * 1998 - Billy Bob Thornton*, A Simple Plan
 * 1999 - Tom Cruise*, Magnolia
 * '2000' - Benicio del Toro, Traffic
 * 2001 - Steve Buscemi, Ghost World
 * 2002 - Dennis Quaid, Far from Heaven
 * '2003' - Tim Robbins, Mystic River
 * 2004 - Thomas Haden Church*, Sideways
 * 2005 - Mickey Rourke, Sin City
 * 2006 - Jackie Earle Haley*, Little Children
 * '2007' - Javier Bardem, No Country for Old Men
 * '2008' - Heath Ledger, The Dark Knight
 * '2009' - Christoph Waltz, Inglourious Basterds
 * '2010' - Christian Bale, The Fighter
 * 2011 - Albert Brooks, Drive
 * 2012 - Philip Seymour Hoffman, The Master
 * '2013' - Jared Leto, Dallas Buyers Club
 * '2014' - J.K. Simmons, Whiplash
 * 2015 - Benicio del Toro, Sicario
 * '2016' - Mahershala Ali, Moonlight
 * 2017 - Willem Dafoe*, The Florida Project
 * 2018 - Richard E. Grant*, Can You Ever Forgive Me?