| AWARD | 1997 | 1998 | 1999 | 2000 |
| BOXER OF THE YEAR | EVANDER HOLYFIELD | ROY JONES, Jr | FELIX TRINIDAD | |
| FIGHT OF THE YEAR | FINITO | ROSENDO ALVAREZ VS. RICHARD "FINITO" LOPEZ | PAULIE AYALA VS. JOHNNY TAPIA | FELIX TRINIDAD VS. FERNANDO VARGAS |
| LEGEND | LARRYHOLME | MICHAEL SPINKS | ||
| PROMOTER OF THE YEAR | DON KING | DON KING PROMOTIONS | DON KING | MURAD MUHAMMAD / DAN GOOSEN |
| OFFICIAL OF THE YEAR | MITCH HALPERN /FERNANDO VISO | STANLEY CHRISTADOULOU | MITCH HALPERN | |
| MANAGER OF THE YEAR | ||||
| JOURNALIST OF THE YEAR | ||||
| COMMENTATOR OF THE YEAR | ||||
| TRAINER OF THE YEAR | LOU DUVA /DON TURNER | FELIX TRINIDAD SR. | ||
| NETWORK OF THE YEAR | SHOWTIME | SHOWTIME | SHOWTIME/ HBO | |
| SITE OF THE YEAR | BALLY'S PARK PLACE CASINO RESORT | PARK PLACE ENTERTAINMENT | ||
| COME BACK OF THE YEAR | VIRGIL HILL | |||
| COMMISSION OF THE YEAR | NEVADA | |||
| LIFETIME ACHIEVEMENT | ||||
| ABUELA DEL AÑO | ||||
| SPONSOR OF THE YEAR | ||||
| BOXER OF THE DECADE | ROY JONES JR. | |||
| ANNOUNCER OF THE YEAR | JIMMY LENNON, Jr | JIMMY LENNON, Jr | JIMMY LENNON, Jr | |
| SPORTS WRITER OF THE YEAR | ||||
| PHOTOGRAPHER OF THE YEAR | ||||
| NEW KID ON THE BLOCK | ||||
| EXECUTIVE OF THE YEAR | DANA JAMISON / BOB GOOD MAN | CELIA TUCKMAN | BOBBY GOODMAN | |
| PROSPECT OF THE YEAR | DAVID REID | |||
| COMMISSIONER | SHIGERU HOJIMA | |||
| MENTION PROMOTER | AKIHIKO HONDA | |||
| NEWEST CHAMPION | DAVID REID | |||
| WBANA HEAVYWEIGHT CHAMPION | JOHN RUIZ | |||
| CURRENT HEAVYWEIGHT CHAMPION | EVANDER HOLYFIELD | JOHNNY RUIZ | ||
| SUPER LAWYERS | PETER FLEMING, Jr /CHARLES LOMAX/ WILLIAM MURPHY, Jr | |||
| PROMOTER OF THE MILLENIUM | DON KING | |||
| BOXER OF THE MILLENIUM | ROY JONES JR. |
