| 2025 | Svea Mutual Insurance Company | 
| 2024 | Belle Prairie Mutual Insurance Company | 
| 2023 | No Award Given | 
| 2022 | Belvidere Mutual Insurance Company | 
| 2021 | Jo Daviess Mutual Insurance Company | 
| 2020 | No Applications received | 
| 2019 | No Applications received | 
| 2018 | West Point Mutual Insurance Company 
 | 
| 2017 | Belvidere Mutual Insurance Company 
 | 
| 2016 | Peru Waltham Mutual Insurance Company | 
| 2015 | Randolph Mutual Insurance Company 
 | 
| 2014 | Heartland Mutual Insurance Company | 
| 2013 | Carthage Mutual Insurance Company | 1995 | Black Hawk Mutual Insurance Company | 
| 2012 | Frontier Mutual Insurance Company | 1994 | Lanark Mutual Insurance Company | 
| 2011 | Payson Mutual Insurance Company | 1993 | Woodford County Mutual Insurance Company | 
| 2010 | LaPrairie Mutual Insurance Company | 1992 | Forreston Mutual Insurance Company | 
| 2009 | Elmira Mutual Insurance Company | 1991 | Bishop Mutual Insurance Company | 
| 2008 | Berlin Mutual Insurance Company | 1990 | Buckeye Mutual Insurance Company | 
| 2007 | Home Farmers Insurance Company | 1989 | Marshall Mutual Insurance Company | 
| 2006 | Town & Country Mutual Insurance Company | 1988 | The Point Mutual Insurance Company | 
| 2005 | Jefferson County Mutual Insurance Company | 1987 | Nashua Mutual Insurance Company | 
| 2004 | Industry Mutual Insurance Company | 1986 | Kane County Mutual Insurance Company | 
| 2003 | Magnolia Evans Mutual Insurance Company | 1985 | Kankakee County Mutual Fire Insurance Company | 
| 2002 | Nokomis Farmers Mutual Insurance Company | 1984 | Rockford Mutual Insurance Company | 
| 2001 | Stockton & Wards Grove Mutual Insurance Company | 1983 | Farmers Pioneer Mutual Fire & Lightning Insurance Company | 
| 2000 | Wilberton Mutual Insurance Company | 1982 | Pontiac Mutual County Fire Insurance Company | 
| 1999 | Central Illinois Mutual Insurance Company | 1981 | Camp Point Mutual Insurance Company | 
| 1998 | Svea Mutual Insurance Company | 1980 | Green Garden Mutual Fire Insurance Company | 
| 1997 | Belleville Mutual Insurance Company | 1979 | Loran Township Mutual Insurance Company | 
| 1996 | Mt. Carroll Mutual Insurance Company | 1978 | Bradford Mutual Fire Insurance Company |