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Illinois
| SPORTSCASTERS | |||
| Year | First | Last | Affiliation, City |
| 2023 | Jason | Benetti | NBC Sports, Chicago |
| 2022 | Jeff | Joniak | Bears Radio Network, Chicago |
| Leila | Rahimi | WMAQ-TV, Chicago | |
| 2021 | Adam | Amin | Bulls/NBC Sports Chicago |
| 2020 | Jason | Benetti | White Sox/NBC Sports Chicago |
| 2019 | Pat | Foley | Blackhawks/NBC Sports Chicago |
| 2018 | Pat | Hughes | Chicago Cubs Radio Network/670 The Score |
| 2017 | Mark | Giangreco | WLS-TV, Chicago |
| 2017 | Pat | Hughes | Chicago Cubs Radio Network/670 The Score |
| 2016 | Len | Kasper | CSN Chicago/WGN/Chicago Cubs |
| 2015 | Pat | Hughes | 780 WBBM Cubs Radio Network, Chicago |
| 2014 | Pat | Hughes | Chicago Cubs |
| 2013 | John | Wiedeman | Chicago Blackhawks/WGN Radio |
| 2012 | Dave | Snell | Bradley University, Peoria |
| 2011 | Dave | Eanet | Northwestern University/WGN Radio |
| 2010 | Mike | Reis | Southern Illinios University |
| 2009 | Pat | Hughes | Chicago Cubs |
| 2008 | Brian | Barnhart | Illinois Sports Network, Champaign |
| 2007 | Pat | Hughes | Chicago Cubs |
| 2006 | Pat | Hughes | Chicago Cubs |
| 2005 | John | Rooney | Chicago White Sox |
| 2004 | Chip | Caray | Chicago Cubs |
| 2003 | Steve | Stone | Chicago Cubs |
| 2002 | Brad | Palmer | WLS-TV, Chicago |
| 2001 | Dave | Snell | Bradley University, Peoria |
| 2000 | Ken | Harrelson | Chicago White Sox |
| 1999 | Pat | Hughes | Chicago Cubs |
| 1998 | Brad | Palmer | WLS-TV, Chicago |
| 1997 | Wayne | Larrivee | WGN-TV/WMAQ, Chicago |
| 1996 | Pat | Hughes | WGN-TV, Chicago |
| 1995 | Brad | Palmer | WLS-TV, Chicago |
| 1994 | Jim | Dore | WLS-TV, Chicago |
| 1993 | Brad | Palmer | WLS-TV, Chicago |
| 1992 | Ken | Harrelson | White Sox, Chicago |
| 1991 | Rich | King | WGN-TV, Chicago |
| 1990 | Jim | Durham | Chicago Bulls |
| 1989 | Jim | Durham | Chicago Bulls |
| 1988 | Brad | Palmer | WLS-TV, Chicago |
| 1987 | Brad | Palmer | WLS-TV, Chicago |
| 1986 | Brad | Palmer | WLS-TV, Chicago |
| 1985 | Harry | Caray | WGN-TV, Chicago |
| 1984 | Harry | Caray | WGN-TV, Chicago |
| 1983 | Harry | Caray | WGN-TV, Chicago |
| 1982 | Brad | Palmer | WBBM, Chicago |
| 1981 | Joe | McConnell | WBBM, Chicago |
| 1980 | Brad | Palmer | WBBM, Chicago |
| 1979 | Jim | Durham | WIND, Chicago |
| 1978 | Harry | Caray | WMAQ, Chicago |
| 1977 | Harry | Caray | WMAQ, Chicago |
| 1976 | Harry | Caray | White Sox Network |
| 1975 | Harry | Caray | WMAQ, Chicago |
| 1974 | Brent | Musburger | WBBM, Chicago |
| 1973 | Harry | Caray | White Sox Network |
| 1972 | Harry | Caray | White Sox Network |
| 1971 | Harry | Caray | White Sox Network |
| 1970 | Brent | Musburger | WBBM, Chicago |
| 1969 | Lloyd | Pettit | WGN-TV, Chicago |
| 1968 | Jack | Brickhouse | WGN-TV, Chicago |
| 1967 | Vince | Lloyd | WGN-TV, Chicago |
| 1966 | Jack | Brickhouse | WGN-TV, Chicago |
| 1965 | Jack | Brickhouse | WGN-TV, Chicago |
| 1964 | Jack | Quinlan | WGN-TV, Chicago |
| 1963 | Jack | Quinlan | WGN-TV, Chicago |
| 1962 | Jack | Quinlan | WGN-TV, Chicago |
| 1961 | Jack | Quinlan | WGN-TV, Chicago |
| 1960 | Jack | Brickhouse | WGN-TV, Chicago |
| 1959 | Jack | Brickhouse | WGN-TV, Chicago |
| SPORTSWRITERS | |||
| Year | First | Last | Affiliation, City |
| 2023 | Kevin | Fishbain | The Athletic, Chicago |
| 2022 | Steve | Greenberg | Chicago Sun-Times, Chicago |
| Mark | Lazerus | The Athletic, Chicago | |
| 2021 | James | Fegan | The Athletic, Chicago |
| 2020 | Shannon | Ryan | Chicago Tribune |
| 2019 | Paul | Sullivan | Chicago Tribune |
| 2018 | Rick | Morrissey | Chicago Sun-Times |
| 2017 | Chris | Hine | Chicago Tribune |
| 2015 | Paul | Sullivan | Chicago Tribune |
| 2015 | Paul | Sullivan | Chicago Tribune |
| 2014 | Rick | Telander | Chicago Sun-Times |
| 2013 | Bruce | Miles | Daily Herald, Arlington Heights |
| 2012 | Dave | Reynolds | Peoria Journal Star |
| 2011 | Paul | Klee | Champaign-Urbana News-Gazette |
| 2010 | Dave | Reynolds | Peoria Journal Star |
| 2010 | Rick | Telander | Chicago Sun-Times |
| 2009 | Dave | Reynolds | Peoria Journal Star |
| 2009 | Rick | Telander | Chicago Sun-Times |
| 2008 | Rick | Telander | Chicago Sun-Times |
| 2007 | Rick | Telander | Chicago Sun-Times |
| 2006 | Mike | Downey | Chicago Tribune |
| 2006 | Rick | Telander | Chicago Sun-Times |
| 2005 | Rick | Telander | Chicago Sun-Times |
| 2004 | Rick | Telander | Chicago Sun-Times |
| 2003 | Mike | Downey | Chicago Tribune |
| 2002 | Rick | Telander | Chicago Sun-Times |
| 2001 | Fred | Kroner | News-Gazette, Champaign |
| 2000 | Skip | Bayless | Chicago Tribune |
| 1999 | Bob | Verdi | Chicago Tribune |
| 1998 | Ron | Pollack | Pro Football Weekly, Bannockburn |
| 1997 | Gene | Wojceichowski | Chicago Tribune |
| 1996 | Bob | Verdi | Chicago Tribune |
| 1995 | Bob | Verdi | Chicago Tribune |
| 1994 | Bob | Verdi | Chicago Tribune |
| 1993 | Don | Pierson | Chicago Tribune |
| 1992 | Bob | Verdi | Chicago Tribune |
| 1991 | Ray | Sons | Sun-Times, Chicago |
| 1990 | Bob | Verdi | Chicago Tribune |
| 1989 | Bob | Verdi | Chicago Tribune |
| 1988 | Joe | Mooshil | Associated Press, Chicago |
| 1987 | Bob | Verdi | Chicago Tribune |
| 1986 | Bob | Verdi | Chicago Tribune |
| 1985 | Bob | Verdi | Chicago Tribune |
| 1984 | Bob | Verdi | Chicago Tribune |
| 1983 | Bob | Verdi | Chicago Tribune |
| 1982 | Bob | Verdi | Chicago Tribune |
| 1981 | Jerome | Holtzman | Chicago Tribune |
| 1980 | Bob | Verdi | Chicago Tribune |
| 1979 | Bob | Verdi | Chicago Tribune |
| 1978 | Bob | Verdi | Chicago Tribune |
| 1977 | Bob | Verdi | Chicago Tribune |
| 1976 | Rick | Talley | Chicago Tribune |
| 1975 | Bob | Verdi | Chicago Tribune |
| 1974 | Robert | Markus | Chicago Tribune |
| 1973 | Bob | Markus | Chicago Tribune |
| 1972 | Robert | Markus | Chicago Tribune |
| 1971 | Rick | Talley | Today, Chicago |
| 1970 | Bill | Gleason | Chicago Sun Times |
| 1969 | Bill | Gleason | Chicago Sun Times |
| 1968 | Bill | Gleason | Chicago Sun Times |
| 1967 | Bill | Gleason | Chicago Sun Times |
| 1966 | John | Carmichael | Chicago Daily News |
| 1965 | Bill | Gleason | Chicago American |
| 1964 | Dave | Condon | Chicago Tribune |
| 1963 | John | Carmichael | Chicago Daily News |
| 1962 | Bert | Bertine | Urbana Courier, Champaign |
| 1961 | John | Carmichael | Chicago Daily News |
| 1960 | John | Carmichael | Chicago Daily News |
| 1959 | John | Carmichael | Chicago Daily News |