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Delaware
| SPORTSCASTERS | |||
| Year | First | Last | Affiliation, City |
| 2023 | Bill | Harman | Blue Hens Radio Network, Newark |
| 2022 | Scott | Klatzkin | Iheart Media, Wilmington |
| 2021 | Gary | Laing | Heritage Sports Radio Network, Hartly |
| 2020 | Scott | Klatzkin | Delaware Sports Properties, Newark |
| 2019 | Scott | Klatzkin | Blue Hens Radio Network/Learfield IMG College, Newark |
| 2018 | Matt | Janus | Wilmington Blue Rocks |
| 2017 | Matt | Janus | Wilmington Blue Rocks |
| 2016 | Scott | Klatzkin | WDSD Radio, Wilmington |
| 2015 | Bill | Harman | 94.7 WDSD, Wilmington |
| 2014 | Matt | Janus | Wilmington Blue Rocks |
| 2013 | Sean | Greene | WDEL Radio, Wilmington |
| 2012 | Scott | Klatzkin | WDSD Radio, Wilmington |
| 2011 | John | Sadak | Wilmington Blue Rocks |
| 2010 | Mike | Corey | WWTXRadio, Wilmington |
| 2009 | Scott | Klatzkin | 1290 The Ticket, New Castle |
| 2009 | John | Sadak | Wilmington Blue Rocks |
| 2008 | Glenn | Frazer | WDSD, Dover |
| 2007 | Omarr | Bashir | Clear Channel Radio, Claymont |
| 2006 | Bill | Komissaroff | KRDX, Claymont |
| 2005 | Mike | Corey | Clear Channel Radio, Claymont |
| 2004 | Omarr | Bashir | WWTX, Claymont |
| 2003 | Mike | Corey | WRDX, Claymont |
| 2002 |
No Winner
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| 2001 |
No Winner
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| 2000 |
No Winner
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| 1999 |
No Winner
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| 1998 |
No Winner
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| 1997 |
No Winner
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| 1996 |
No Winner
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| 1995 |
No Winner
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| 1994 | Jim | Hayes | First State News, New Castle |
| 1993 |
No Winner
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| 1992 | Jim | Hayes | TCI Cablevision, New Castle |
| 1991 | Jim | Hayes | WNS-TV, New Castle |
| 1990 | Jim | Hayes | Heritage Cablevision, New Castle |
| 1989 | Martin | Feurer | Heritage Cablevision, New Castle |
| 1988 | Martin | Feurer | WNS-TV, New Castle |
| 1987 | Martin | Feurer | WNS-TV, Newark |
| 1987 | Bill | Pheiffer | WDEL, Wilmington |
| 1986 | Martin | Feurer | WILM, Wilmington |
| 1985 | Jon | Warner | WNS, New Caster |
| 1984 | Marty | Feurer | WILM, Wilmington |
| 1983 | Bob | Kelly | WILM, Wilmington |
| 1982 | Bob | Kelly | WILM, Wilmington |
| 1981 | Bill | Pheiffer | WDEL, Wilmington |
| 1980 | Bob | Kelly | WILM, Wilmington |
| 1979 | Bob | Kelly | WILM, Wilmington |
| 1979 | Bill | Pheiffer | WDEL, Wilmington |
| 1978 | Bob | Kelly | WILM, Wilmington |
| 1977 | Bob | Kelly | WILM, Wilmington |
| 1976 | Bob | Kelly | WILM, Wilmington |
| 1975 | Bill | Pheiffer | WDEL, Wilmington |
| 1974 | Bob | Kelly | WILM, Wilmington |
| 1973 | Bill | Pheiffer | WDEL, Wilmington |
| 1972 | Bob | Kelly | WILM, Wilmington |
| 1971 | Bob | Kelly | WILM, Wilmington |
| 1970 | Bob | Kelly | WILM, Wilmington |
| 1969 | Bob | Kelly | WILM, Wilmington |
| 1968 | Dick | Graham | WDEL, Wilmington |
| 1967 | Bob | Kelly | WILM, Wilmington |
| 1966 | Bob | Kelly | WILM, Wilmington |
| 1965 | Bob | Kelly | WILM, Wilmington |
| 1964 | Bob | Kelly | WILM, Wilmington |
| 1963 | Bryan | Field | WDEL, Wilmington |
| 1962 | Bob | Kelly | WDEL, Wilmington |
| 1961 | Bob | Kelly | WDEL, Wilmington |
| 1960 | Bryan | Field | WDEL, Wilmington |
| 1959 | Bob | Kelly | WDEL, Wilmington |
| SPORTSWRITERS | |||
| Year | First | Last | Affiliation, City |
| 2023 | Kevin | Tresolini | The News Journal, Wilmington |
| 2022 | Brad | Myers | The News Journal, Wilmington |
| 2021 | Kevin | Tresolini | News Journal, Wilmington |
| 2020 | Martin | Frank | News Journal, Wilmington |
| 2019 | Kevin | Tresolini | News Journal, Wilmington |
| 2018 | Andy | Walter | Delaware State News |
| 2017 | Kevin | Tresolini | News Journal, Wilmington |
| 2016 | Kevin | Tresolini | News Journal, Wilmington |
| 2015 | Kevin | Tresolini | News Journal, Wilmington |
| 2014 | Brad | Myers | News Journal, Wilmington |
| 2013 | Andy | Walter | Delaware State News, Dover |
| 2012 | Andy | Walter | Delaware State News, Dover |
| 2011 | Jon | Buzby | Newark Post, Newark |
| 2010 | Martin | Frank | News Journal, Wilmington |
| 2009 | Kevin | Tresolini | News Journal, Wilmington |
| 2008 | Andy | Walter | Delaware State News, Dover |
| 2007 | Kevin | Tresolini | The News Journal, Wilmington |
| 2006 | Kevin | Tresolini | The News Journal, Wilmington |
| 2005 | Kevin | Noonan | The News Journal, Wilmington |
| 2004 | Kevin | Tresolini | The News Journal, New Castle |
| 2003 | Kevin | Tresolini | The News Journal, Wilmington |
| 2002 | No Winner | ||
| 2001 | No Winner | ||
| 2000 | No Winner | ||
| 1999 | No Winner | ||
| 1998 | No Winner | ||
| 1997 | No Winner | ||
| 1996 | No Winner | ||
| 1995 | Kevin | Tresolini | The News Journal, Wilmington |
| 1994 | Kevin | Tresolini | The News Journal, Wilmington |
| 1993 | No Winner | ||
| 1992 | Tom | Tomashek | News Journal, Wilmington |
| 1991 | Tom | Tomashek | News Journal, Wilmington |
| 1990 | Tom | Tomashek | News Journal, Wilmington |
| 1989 | Jack | Chevalier | News Journal, Wilmington |
| 1988 | Kevin | Noonan | News Journal, Wilmington |
| 1987 | Tom | Tomashek | News Journal, Wilmington |
| 1987 | Kevin | Tresolini | News Journal, Wilmington |
| 1986 | Tom | Tomashek | News Journal, Wilmington |
| 1985 | Ray | Finocchiaro | News Journal, Wilmington |
| 1984 | Matt | Zabitka | Wilmington News-Journal |
| 1983 | Israel | Katzman | Wilmington News-Journal |
| 1982 | George | Hammond | Delaware State News, Dover |
| 1981 | Scott | Wasser | State News, Dover |
| 1980 | Tom | Tomashek | Wilmington News-Journal |
| 1979 | Hal | Bodley | Wilmington News-Journal |
| 1978 | Hal | Bodley | Wilmington News-Journal |
| 1977 | Matt | Zabitka | Wilmington News-Journal |
| 1976 | Matt | Zabitka | Wilmington News-Journal |
| 1975 | Hal | Bodley | Wilmington News-Journal |
| 1974 | Hal | Bodley | Wilmington News-Journal |
| 1973 | Hal | Bodley | Wilmington News-Journal |
| 1972 | William | Schellhammer | Wilmington News-Journal |
| 1971 | William | Schellhammer | Wilmington News-Journal |
| 1970 | Hal | Bodley | Wilmington News-Journal |
| 1969 | Hal | Bodley | Wilmington News-Journal |
| 1968 | Hal | Bodley | Wilmington News-Journal |
| 1967 | Hal | Bodley | Wilmington News-Journal |
| 1966 | Albert | Cartwright | Wilmington News-Journal |
| 1965 | Hal | Bodley | Wilmington News-Journal |
| 1964 | Albert | Cartwright | Wilmington News-Journal |
| 1963 | Hal | Bodley | Wilmington News-Journal |
| 1962 | Izzy | Katzman | Wilmington Evening Journal |
| 1961 | Hal | Bodley | Wilmington News-Journal |
| 1960 | Albert | Cartwright | The Journal, Wilmington |
| 1959 | Albert | Cartwright | Wilmington News |