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- Bear Bryant Awards
- The Annie (Ann Spencer Sports Connector Award)
Massachusetts
| SPORTSCASTERS | |||
| Year | First | Last | Affiliation, City |
| 2024 | Jack | Edwards | Bruins/NESN, Boston |
| 2023 | Mike | Gorman | Celtics TV Network, Boston |
| 2022 | Joe | Castiglione | Red Sox Radio Network, Boston |
| 2021 | Bob | Socci | Patriots Radio Network/98.5 the Sports Hub, Boston |
| 2020 | Joe | Amorosino | WHDH-TV, Boston |
| 2020 | Dan | Roche | WBZ-TV, Boston |
| 2019 | Jerry | Remy | Red Sox/NESN |
| 2018 | Mike | Gorman | Boston Celtics/NBC Sports Boston |
| 2017 | Dan | Roche | WBZ-TV, Boston |
| 2016 | Joe | Amorosino | WHDH-TV, Boston |
| 2016 | Mike | Gorman | Celtics TV/CSN New England, Boston |
| 2015 | Don | Orsillo | NESN, Boston |
| 2014 | Dave | Goucher | Bruins Radio Network/98.5 The Sports Hub |
| 2014 | Dan | Roche | WBZ-TV, Boston |
| 2013 | Dave | Goucher | Bruins Radio Network/98.5 The Sports Hub |
| 2012 | Mike | Lynch | WCVB-TV, Needham |
| 2011 | Mike | Lynch | WCVB-TV, Needham |
| 2010 | Mike | Lynch | WCVB-TV, Needham |
| 2009 | Mike | Lynch | WCVB-TV, Needham |
| 2008 | Mike | Lynch | WCVB-TV, Needham |
| 2007 | Mike | Lynch | WCVB-TV, Needham |
| 2006 | Mike | Lynch | WCVB-TV, Needham |
| 2005 | Don | Orsillo | New England Sports Network, Boston |
| 2004 | Jerry | Remy | NESN-TV, Boston |
| 2003 | Mike | Lynch | WCVB, Boston |
| 2002 | Bob | Lobel | WBZ, Boston |
| 2001 | Bob | Lobel | WBZ, Boston |
| 2000 | Bob | Lobel | WBZ, Boston |
| 1999 | Mike | Lynch | WCVB, Boston |
| 1998 | Gene | Lavanchy | WHDH-TV, Boston |
| 1997 | Bob | Lobel | WBZ, Boston |
| 1996 | Scott | Wahle | WBZ, Boston |
| 1995 | Bob | Lobel | WBZ, Boston |
| 1994 | Bob | Lobel | WBZ, Boston |
| 1993 | Bob | Lobel | WBZ, Boston |
| 1992 | Bob | Lobel | WBZ, Boston |
| 1991 | Mike | Lynch | WHDH-TV, Boston |
| 1990 | Mike | Lynch | WHDH-TV, Boston |
| 1989 | Mike | Lynch | WCVB, Boston |
| 1988 | Mike | Lynch | WCVB, Needham |
| 1987 | Mike | Lynch | WCVB, Boston |
| 1986 | Mike | Lynch | WCVB, Needham |
| 1985 | Mike | Lynch | WCVB, Boston |
| 1984 | Bob | Lobel | WBZ, Boston |
| 1984 | Gil | Santos | WBZ, Boston |
| 1983 | Bob | Lobel | WBZ, Boston |
| 1982 | Bob | Lobel | WBZ, Boston |
| 1981 | Gil | Santos | WBZ, Boston |
| 1980 | Gil | Santos | WBZ, Boston |
| 1979 | Clark | Booth | WCVB, Boston |
| 1978 | Ned | Martin | WITS, Boston |
| 1977 | Clark | Booth | WCVB, Boston |
| 1976 | Ned | Martin | WHDH, Boston |
| 1975 | Clark | Booth | WCVB, Boston |
| 1974 | Ned | Martin | WHDH, Boston |
| 1973 | Ned | Martin | WHDH, Boston |
| 1972 | Ned | Martin | Red Sox Network |
| 1971 | Don | Gillis | WCVB, Boston |
| 1970 | Don | Gillis | WHDH, Boston |
| 1969 | Don | Gillis | WHDH, Boston |
| 1968 | Don | Gillis | WHDH, Boston |
| 1967 | Don | Gillis | WHDH, Boston |
| 1966 | Don | Gillis | WHDH, Boston |
| 1965 | Don | Gillis | WHDH, Boston |
| 1964 | Don | Gillis | WHDH, Boston |
| 1963 | Curt | Gowdy | WHDH, Boston |
| 1962 | Curt | Gowdy | WHDH, Boston |
| 1961 | Curt | Gowdy | WHDH, Boston |
| 1960 | Curt | Gowdy | WHDH, Boston |
| 1959 | Curt | Gowdy | WHDH, Boston |
| SPORTSWRITERS | |||
| Year | First | Last | Affiliation, City |
| 2024 | Adam | Himmelsbach | Boston Globe, Boston |
| 2023 | Alex | Speier | Boston Globe, Boston |
| 2022 | Karen | Guregian | Boston Herald, Boston |
| 2021 | Kevin | Dupont | The Boston Globe |
| 2020 | Peter | Abraham | The Boston Globe |
| 2019 | Dan | Shaughnessy | The Boston Globe |
| 2019 | Mike | Reiss | ESPN.com, Boston |
| 2018 | Dan | Shaughnessy | The Boston Globe |
| 2017 | Dan | Shaughnessy | The Boston Globe |
| 2016 | Kevin | Dupont | The Boston Globe |
| 2015 | Steve | Buckley | Boston Herald |
| 2015 | Kevin | Dupont | The Boston Globe |
| 2014 | Nick | Cafardo | The Boston Globe |
| 2014 | Kevin | Dupont | The Boston Globe |
| 2013 | Kevin | Dupont | The Boston Globe |
| 2012 | Dan | Shaughnessy | The Boston Globe |
| 2011 | Dan | Shaughnessy | The Boston Globe |
| 2010 | Bob | Ryan | The Boston Globe |
| 2009 | Dan | Shaughnessy | The Boston Globe |
| 2008 | Tony | Massarotti | The Boston Globe |
| 2007 | Dan | Shaughnessy | The Boston Globe |
| 2006 | Bob | Ryan | The Boston Globe |
| 2005 | Ron | Borges | The Boston Globe |
| 2004 | Kevin | Dupont | The Boston Globe |
| 2003 | Ron | Borges | The Boston Globe |
| 2002 | Ron | Borges | The Boston Globe |
| 2001 | Bob | Ryan | The Boston Globe |
| 2000 | Tony | Massarotti | Boston Herald-Traveler |
| 1999 | Michael | Madden | The Boston Globe |
| 1998 | Ron | Borges | The Boston Globe |
| 1997 | Bob | Ryan | The Boston Globe |
| 1996 | Dan | Shaughnessy | The Boston Globe |
| 1995 | Dan | Shaughnessy | The Boston Globe |
| 1994 | Dan | Shaughnessy | The Boston Globe |
| 1993 | Dan | Shaughnessy | The Boston Globe |
| 1992 | Dan | Shaughnessy | The Boston Globe |
| 1991 | Dan | Shaughnessy | The Boston Globe |
| 1990 | Dan | Shaughnessy | The Boston Globe |
| 1989 | Will | McDonough | The Boston Globe |
| 1988 | Tim | Horgan | Boston Herald |
| 1987 | Will | McDonough | The Boston Globe |
| 1986 | Tim | Horgan | Boston Herald-Traveler |
| 1986 | Will | McDonough | The Boston Globe |
| 1985 | Will | McDonough | Boston Globe |
| 1984 | Leigh | Montville | Boston Globe |
| 1983 | Will | McDonough | Boston Globe |
| 1982 | Tim | Horgan | Boston Herald-Traveler |
| 1981 | Ray | Fitzgerald | Boston Globe |
| 1980 | Ray | Fitzgerald | Boston Globe |
| 1979 | Ray | Fitzgerald | Boston Globe |
| 1978 | Ray | Fitzgerald | Boston Globe |
| 1977 | Ray | Fitzgerald | Boston Globe |
| 1976 | Ray | Fitzgerald | Boston Globe |
| 1975 | Ray | Fitzgerald | Boston Globe |
| 1974 | Ray | Fitzgerald | Boston Globe |
| 1973 | Ray | Fitzgerald | Boston Globe |
| 1972 | Ray | Fitzgerald | Boston Globe |
| 1971 | Tim | Horgan | Boston Herald-Traveler |
| 1970 | Ray | Fitzgerald | The Globe, Boston |
| 1969 | Tim | Horgan | Boston Herald-Traveler |
| 1968 | Tim | Horgan | Boston Herald-Traveler |
| 1967 | Tim | Horgan | Boston Herald-Traveler |
| 1966 | John | Gillooly | Boston Record |
| 1965 | Harold | Kaese | The Boston Globe |
| 1964 | Tim | Horgan | Boston Traveler |
| 1963 | Ray | Fitzgerald | The Springfield Union |
| 1962 | John | Gillooly | Boston Record American |
| 1961 | John | Gillooly | Boston Record American |
| 1960 | Jim | Reagan | The Daily News, Springfield |
| 1959 | John | Gillooly | Boston Record |