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District of Columbia
| SPORTSCASTERS | |||
| Year | First | Last | Affiliation, City |
| 2022 | Grant | Paulsen | 106.7 The Fan, Washington |
| 2021 | Joe | Beninati | Washington Capitals/NBC Sports Network, Washington |
| 2020 | Dave | Jageler | Nationals Radio Network, Washington |
| 2020 | John | Walton | Capitals Radio Network, Washington |
| 2019 | Dave | Johnson | Wizards/WTOP Radio/NBC 4/DC United, Washington |
| 2018 | Steve | Buckhantz | Wizards/NBC Sports Washington |
| 2017 | Joe | Beninati | Washington Capitals/NBC Sports Washington |
| 2016 | Grant | Paulsen | WJFK/106.7 The Fan, Washington |
| 2016 | George | Wallace | WTOP Radio |
| 2015 | George | Wallace | WTOP Radio |
| 2014 | Joe | Beninati | Comcast Sports Net |
| 2014 | Bob | Carpenter | MASN/Washington Nationals |
| 2013 | Tim | Brant | WJLA-TV |
| 2012 | Chick | Hernandez | CSN Mid-Atlantic |
| 2011 | Lindsay | Czarniak | WRC-TV |
| 2010 | Chris | Miller | Comcast Sports Net |
| 2010 | Dave | Feldman | WTTG-TV |
| 2009 |
No Winner
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| 2008 |
No Winner
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| 2007 |
No Winner
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| 2006 |
No Winner
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| 2005 |
No Winner
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| 2004 |
No Winner
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| 2003 |
No Winner
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| 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 |
No Winner
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| 1993 |
No Winner
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| 1992 |
No Winner
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| 1991 | Glenn | Brenner | WUSA TV |
| 1990 | Glenn | Brenner | WUSA TV |
| 1989 | Frank | Herzog | WJLA TV |
| 1988 | Glenn | Brenner | WUSA TV |
| 1987 | Frank | Herzog | WJLA TV |
| 1986 | Frank | Herzog | WJLA TV |
| 1985 | Frank | Herzog | WJLA TV |
| 1984 | Frank | Herzog | WJLA TV |
| 1983 | Frank | Herzog | WJLA TV |
| 1982 | Frank | Herzog | WDVM |
| 1981 | Frank | Herzog | WDVM |
| 1980 | Frank | Herzog | WDVM |
| 1979 | Tony | Roberts | WRC |
| 1978 | Tony | Roberts | WRC |
| 1977 | Tony | Roberts | WRC |
| 1976 | Tony | Roberts | WRC |
| 1975 | Tony | Roberts | WWDC |
| 1974 | Tony | Roberts | WWDC |
| 1973 | Warner | Wolf | WTOP |
| 1972 | Warner | Wolf | WTOP |
| 1971 | Maury | Povich | WTTG |
| 1970 | Dan | Daniels | WRC |
| 1969 | Dan | Daniels | WRC |
| 1968 | Steve | Gilmartin | WMAL |
| 1967 | Dan | Daniels | WTOP |
| 1966 | Bill | McColgan | WTOP |
| 1965 | Dan | Daniels | WTOP |
| 1964 | Jim | Simpson | WRC |
| 1963 | Bill | McColgan | WTOP |
| 1962 | Jim | Simpson | WRC |
| 1961 | Bill | McColgan | WTOP |
| 1960 | Jim | Simpson | WRC |
| 1959 | Jim | Simpson | WRC |
| SPORTSWRITERS | |||
| Year | First | Last | Affiliation, City |
| 2022 | Barry | Svrluga | Washington Post, Washington |
| 2021 | Mark | Zuckerman | MASNSports.com |
| 2020 | Barry | Svrulga | Washington Post |
| 2019 | Brittany | Ghiroli | The Athletic, Washington |
| 2018 | Barry | Svrluga | Washington Post |
| 2017 | Mark | Zuckerman | MASNSports.com |
| 2016 | Barry | Svrulga | Washington Post |
| 2015 | Barry | Svrulga | Washington Post |
| 2014 | Thom | Loverro | Washington Times |
| 2013 | Mike | Harris | Washington Times |
| 2012 | Brian | McNally | Washington Examiner |
| 2011 | John | Keim | Washington Examiner |
| 2010 | Rick | Snider | Washington Examiner |
| 2010 | Dan | Steinberg | Washington Post |
| 2009 | No Winner | ||
| 2008 | No Winner | ||
| 2007 | No Winner | ||
| 2006 | No Winner | ||
| 2005 | No Winner | ||
| 2004 | No Winner | ||
| 2003 | No Winner | ||
| 2002 | No Winner | ||
| 2001 | No Winner | ||
| 2000 | No Winner | ||
| 1999 | No Winner | ||
| 1998 | No Winner | ||
| 1997 | No Winner | ||
| 1996 | No Winner | ||
| 1995 | No Winner | ||
| 1994 | No Winner | ||
| 1993 | No Winner | ||
| 1992 | No Winner | ||
| 1991 | Richard | Justice | The Washington Post |
| 1990 | Tony | Kornheiser | The Washington Post |
| 1989 | Richard | Justice | The Washington Post |
| 1988 | Richard | Justice | The Washington Post |
| 1987 | John | Feinstein | The Washington Post |
| 1986 | John | Feinstein | The Washington Post |
| 1985 | John | Feinstein | The Washington Post |
| 1984 | Tom | Boswell | The Washington Post |
| 1983 | Dave | Kindred | The Post |
| 1982 | Dave | Kindred | The Post |
| 1981 | Dave | Kindred | The Post |
| 1980 | Dave | Kindred | The Post |
| 1979 | Dave | Kindred | The Post |
| 1978 | Ken | Denlinger | The Post |
| 1977 | Steve | Hershey | The Evening Star |
| 1976 | Steve | Hershey | The Evening Star |
| 1975 | Steve | Guback | The Washington Star |
| 1974 | Ken | Denlinger | The Post |
| 1973 | Leonard | Shapiro | The Post |
| 1972 | Shirley | Povich | The Post |
| 1971 | Gerry | Strine | The Post |
| 1970 | Ken | Denlinger | The Post |
| 1969 | George | Minot, Jr. | The Washington Post |
| 1968 | Walter | Haight | The Washington Post |
| 1967 | William | Gildea | The Washington Post |
| 1966 | Dave | Brady | The Washington Post |
| 1965 | Shirley | Povich | The Washington Post |
| 1964 | Francis | Stann | The Evening Star |
| 1963 | Shirley | Povich | The Washington Post |
| 1962 | Rod | Thomas | The Evening Star |
| 1961 | Francis | Stann | The Washington Star |
| 1960 | Merrell | Whittlesey | The Evening Star |
| 1959 | Burton | Hawkins | Washington Star |