The Toqued Warrior: The Real Popes of Chilitown
| 1967 | Wick Fowler & H. Allen Smith |
| 1968 | no winner named |
| 1969 | C.V. Wood, Jr. |
| 1970 | Wick Fowler |
| 1971 | C.V. Wood, Jr. |
| 1972 | Howard Winsor |
| 1973 | Joe DeFrates |
| 1974 | Allegani Jani Schofield |
| 1975 | Joe DeFrates (ISC) Susie Watson (CASI) |
| 1976 | Rudy Valdez (ISC) Albert S. Agnor (CASI) |
| 1977 | Jay Pennington (ISC) Tom Griffin (CASI) |
| 1978 | Laverne Harris (ISC) Richard Simon (CASI) |
| 1979 | Joe & Shirley Stewart (ISC) Wayland Walker (CASI) |
| 1980 | Bill Pfeiffer (ISC) Bob Moore (CASI) |
| 1981 | Fred & Linda Drexel (ISC) Bill Douglas (CASI) |
| 1982 | Bill Pfeiffer (ISC) Tom Skipper (CASI) |
| 1983 | Harold Timber (ISC) Paul Brian (CASI) |
| 1984 | Dusty Hudspeth (ISC) Steve Weaver (CASI) |
| 1985 | Carol & Dave Hancock (ISC) Wes Ritchey (CASI) |
| 1986 | Jim Beaty (ISC) Bobby Aldridge (CASI) |
| 1987 | Margo Knudson (ISC) David Henson (CASI) |
| 1988 | Kenton Stafford (ISC) Lynn Hejtmancik (CASI) |
| 1989 | Philip M. Walter (ISC) Barbara Britton (CASI) |
| 1990 | David Valega (ISC) Jerry Hunt (CASI) |
| 1991 | Randy Robinson (ISC) Doris Coats (CASI) |
| 1992 | Ed Pierczynski (ISC) Cindy Reed (CASI) |
| 1993 | Cathy R. Wilkey (ISC) Cindy Reed (CASI) |
| 1994 | Bill Ray (ISC) Jim Hedrick (CASI) |
| 1995 | Norm Gaul (ISC) Colleen Wallace (CASI) |
| 1996 | Georgia Weller (ISC) Bo Prewitt (CASI) |
| 1997 | Steve Falkowski (ISC) Glenn Dickey (CASI) |
| 1998 | Kathy LeGear (ISC) Carol West (CASI) |
| 1999 | Maud Swick (ISC) Bob Coats (CASI) |
| 2000 | Jim Weller (ISC) Dixie Johnson (CASI) |
| 2001 | George Swick (ISC) Randy Moore (CASI) |
| 2002 | Ron Burt (ISC) Pat Pilchiek (CASI) |
| 2003 | Bob Wetzel (ISC) Honey Jones (CASI) |
| 2004 | Kathleen Hipskind (ISC) Roger Foltz (CASI) |
| 2005 | Doug Wilkey (ISC) Margaret Nadeau (CASI) |
| 2006 | J.R. Knudson (ISC) Dana Plocheck (CASI) |
| 2007 | Jerry Buma (ISC) Debbie Ashman (CASI) |
| 2008 | Georgia Weller (ISC) Susan Dean (CASI) |
| 2009 | Maureen Barrett (ISC) Margaret Nadeau (CASI) |
| 2010 | Thomas H. Hoover, Jr. (ISC) Tom Dozier (CASI) |





