SPORTSCASTERS
| YEAR | FIRST NAME | LAST NAME | AFFILIATION |
| 2025 | Kanoa | Leahey | Spectrum Sports, Honolulu |
| 2024 | Rob | Demallo | KHON-TV, Honolulu |
| 2023 | Kanoa | Leahey | Spectrum Sports, Honolulu |
| 2022 | Rob | DeMello | KHON-TV, Honolulu |
| 2021 | Alan | Hoshida | KHON-TV, Honolulu |
| 2020 | Rob | DeMello | KHON-TV, Honolulu |
| 2019 | Bobby | Curran | ESPN Honolulu |
| 2018 | Kanoa | Leahey | Spectrum Sports/ESPN 900 |
| 2017 | Kanoa | Leahey | Spectrum Sports/ESPN 900, Honolulu |
| 2016 | Rob | DeMello | KHON-TV, Honolulu |
| 2015 | Rob | DeMello | KHON-TV, Honolulu |
| 2014 | No Winner | ||
| 2013 | No Winner | ||
| 2012 | No Winner | ||
| 2011 | Dave | Vinton | OC 16, Honolulu |
| 2011 | No Winner | ||
| 2010 | Dave | Vinton | OC 16, Honolulu |
| 2009 | Bobby | Curran | KKEA, Honolulu |
| 2008 | Bobby | Curran | KKEA, Honolulu |
| 2007 | Bobby | Curran | KKEA, Honolulu |
| 2006 | Bobby | Curran | KKEA, Honolulu |
| 2005 | Bobby | Curran | KKEA, Honolulu |
| 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 | Dave | Vinton | KGMB, Honolulu |
| 1995 | No Winner | ||
| 1994 | Scott | Culbertson | KGMB, Honolulu |
| 1993 | No Winner | ||
| 1992 | No Winner | ||
| 1991 | Jim | Leahey | KHNL-TV, Honolulu |
| 1990 | Jim | Leahey | KHNL-TV, Honolulu |
| 1989 | Jim | Leahey | KHNL-TV, Honolulu |
| 1988 | Jim | Leahey | KHNL-TV, Honolulu |
| 1987 | Jim | Leahey | KHNL-TV, Honolulu |
| 1986 | Jim | Leahey | KHNL-TV, Honolulu |
| 1985 | Jim | Leahey | KKUA/KHNL, Honolulu |
| 1984 | Jim | Leahey | KKUA, Honolulu |
| 1983 | Rick | Quan | KITV, Honolulu |
| 1982 | Jim | Leahey | KGMB-TV, Honolulu |
| 1981 | Jim | Leahey | KGMB-TV, Honolulu |
| 1980 | Jim | Leahey | KGMB-TV, Honolulu |
| 1979 | Jim | Leahey | KGO, Honolulu |
| 1978 | Chris | Allen | KGU, Honolulu |
| 1977 | Chris | Allen | KGU, Honolulu |
| 1976 | Ken | Wilson | KGU, Honolulu |
| 1975 | Jim | Leahey | KGU, Honolulu |
| 1974 | Jim | Leahey | KITV, Honolulu |
| 1973 | Jim | Leahey | KITV, Honolulu |
| 1972 | Jim | Leahey | KGU, Honolulu |
| 1971 | Jim | Leahey | KGU, Honolulu |
| 1970 | Al | Michaels | KGMB-TV, Honolulu |
| 1969 | Al | Michaels | KGU/KHVH-TV, Honolulu |
| 1968 | Al | Michaels | KGU, Honolulu |
| 1967 | Jim | Lathrop | KGMB-TV, Honolulu |
| 1966 | Chuck | Leahey | KGMB-TV, Honolulu |
| 1965 | Frank | Valenti | KGMB-TV, Honolulu |
| 1964 | Frank | Valenti | KGMB-TV, Honolulu |
| 1963 | Chuck | Leahey | KGU, Honolulu |
| 1962 | Harry | Kalas | Honolulu |
| 1961 | Frank | Valenti | KGMB-TV, Honolulu |
SPORTSWRITERS
| YEAR | FIRST NAME | LAST NAME | AFFILIATION |
| 2025 | Stephen | Tsai | Star-Advertiser, Honolulu |
| 2024 | Billy | Hull | Honolulu Star Advertiser, Honolulu |
| 2023 | Brian | McInnis | Spectrum News Hawaii, Honolulu |
| 2022 | Jason | Kaneshiro | Honolulu Star-Advertiser, Honolulu |
| 2021 | Rob | Collias | Maui News, Wailuku |
| 2020 | Stephen | Tsai | Honolulu Star Advertiser |
| 2019 | Stephen | Tsai | Honolulu Star Advertiser |
| 2018 | Stephen | Tsai | Honolulu Star Advertiser |
| 2017 | Stephen | Tsai | Honolulu Star Advertiser |
| 2016 | Brian | McInnis | Honolulu Star Advertiser |
| 2015 | Billy | Hull | Honolulu Star Advertiser |
| 2014 | No Winner | ||
| 2013 | No Winner | ||
| 2012 | No Winner | ||
| 2011 | Stephen | Tsai | Honolulu Advertiser |
| 2010 | Wes | Nakama | Honolulu Advertiser |
| 2009 | T.V. | Mott | Maui Weekly, Kenei |
| 2009 | Stephen | Tsai | Honolulu Advertiser |
| 2008 | T.V. | Mott | Maui Weekly, Kenei |
| 2007 | No Winner | ||
| 2006 | Ferd | Lewis | The Advertiser, Honolulu |
| 2005 | Dave | Reardon | Honolulu Star-Bulletin |
| 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 | Stephen | Tsai | The Advertiser, Honolulu |
| 1995 | No Winner | ||
| 1994 | Ferd | Lewis | The Advertiser, Honolulu |
| 1993 | No Winner | ||
| 1992 | No Winner | ||
| 1991 | Stephen | Tsai | The Advertiser, Honolulu |
| 1990 | No Winner | ||
| 1989 | Ferd | Lewis | The Advertiser, Honolulu |
| 1988 | Dave | Koga | The Advertiser, Honolulu |
| 1987 | Paul | Carbalho | Honolulu Star-Bulletin |
| 1986 | Paul | Carvalho | Honolulu Star-Bulletin |
| 1985 | Dave | Koga | The Advertiser, Honolulu |
| 1984 | Andy | Yamaguchi | The Advertiser, Honolulu |
| 1983 | Ferd | Lewis | The Advertiser, Honolulu |
| 1982 | Clyde | Mizumoto | The Advertiser, Honolulu |
| 1981 | Dick | Couch | Honolulu Star-Bulletin |
| 1981 | Ferd | Lewis | The Advertiser, Honolulu |
| 1980 | Dick | Couch | Honolulu Star-Bulletin |
| 1979 | Steve | Kimura | The Advertiser, Honolulu |
| 1978 | Dick | Fishback | The Advertiser, Honolulu |
| 1977 | Dick | Fishback | The Advertiser, Honolulu |
| 1976 | Mark | Matsunaga | The Advertiser, Honolulu |
| 1975 | Daniel | McGuire | The Advertiser, Honolulu |
| 1974 | Monte | Ito | The Advertiser, Honolulu |
| 1973 | Dick | Couch | Honolulu Star-Bulletin |
| 1972 | Dick | Couch | Honolulu Star-Bulletin |
| 1971 | Jim | Hackleman | Honolulu Star-Bulletin |
| 1970 | Dan | McGuire | The Advertiser, Honolulu |
| 1969 | Jim | Hackleman | Honolulu Star-Bulletin |
| 1968 | Ferd | Borsch | The Advertiser, Honolulu |
| 1967 | Dan | McGuire | The Advertiser, Honolulu |
| 1966 | Tom | Hopkins | Honolulu Star-Bulletin |
| 1965 | Hal | Wood | The Advertiser, Honolulu |
| 1964 | Bill | Kwon | Honolulu Star-Bulletin |
| 1963 | Bill | Gee | Honolulu Star-Bulletin |
| 1962 | Monte | Ito | The Advertiser, Honolulu |
| 1961 | Ferd | Borsch | Honolulu Advertiser |