Rededicated to Block Island Race Week in 1991, to the overall winner of the largest one-design class.

1991 – Touch of Grey – C. Gowrie & T. Goss – J35
1993 – Begnal – Dan Neri – J35
1995 – Inside Trader – Trevor Underwood – J35
1997 – USA 48 – Barry Allardice & Ed Collins – Mumm 30
1999 – Eclipse – Damian Emery – J105
2001 – PFM2 – John Hourihan – J105
2003 – Pretty Sketchy – Thomas Enright – J105
2005 – Pretty Sketchy – Thomas Enright – J105
2007 – Savasana – Brian Keane – J105
2009 – Power Play – Bruce Stone & Scott deWeese – J105
2011 – Rush – Bill Sweetser – J109
2013 – Storm – Rick Lyall – J109
2015 – Caminos – Donald Filippelli – J109
2017 – Loki – David Rosow – J109
2019 – Lou Lou – Paul Beaudin – J105

2021 – Emoticon – Jonathan Rechtschaffer – J109