| YEAR | GRAND MARSHAL | QUEEN |
| 2001 | MARY REYNOLDS | |
| 2002 | MARGARITA BERGEN | |
| 2003 | MARY KATHERINE LONATRA TUSA | DEBBIE GAGNE |
| 2004 | ROBERT MONDAVI ROBERT MONDAVI WINERY |
MARY ANNE MCDOUGAL |
| 2005 | STEVE REEDER SIMI WINES |
KATHERINE BISHOP |
| 2006 | JEAN NOEL FOURMEAUX du SARTEL CHATEAU POTELLE |
ANNIE LEWIS |
| 2007 | MARCHESI FERDINANDO FRESCABALDI FRESCABALDI WINES, ITALY |
GILLIAN PIERCE |
| 2008 | LARRY MAGUIRE FARNIENTE WINERY |
SAMARA POCHE |
| 2009 | BARRY WISS TRINCHERO FAMILY ESTATES |
MELANIE TALIA |
| 2010 | CLOVIS TATTINGER, TATTINGER CHAMPAGNE, FRANCE |
ALL FORMER QUEENS |
| 2011 | JOHN CONOVER PLUMPJACK & CADE WINERY |
YVETTE DEBLANC |
| 2012 | JEAN NOEL FOURMEAUX du SARTEL CHATEAU POTELLE |
ALLYSON CABES |
| 2013 | JEAN CHARLES BOISSET BOISETT FAMILY ESTATES |
GAIL CAVETT |
| 2014 | GEORGE SANDEMAN SANDEMAN PORT WINE, PORTUGAL |
AMY BORRELL |
| 2015 | AGUSTIN HUNEEUS HUNEEUS VINTNERS |
JEFFREY MCILWAIN |
| 2016 | CARLO TRINCHERO & JOSH PHELPS TAKEN WINE COMPANY |
KELLY VAUGHN |
| 2017 | JUSTIN BALDWIN JUSTIN WINES |
SARAH BLOSCH |
| 2018 | ANDREW BROWNE PRECEPT WINES |
PAULETTE SLONE |
| 2019 | KIMBERLEE NICHOLS MARKHAM VINEYARD |
GAYLE DELLINGER |
| 2020 | CHARLES SMITH | ALL FORMER QUEENS |