From 2014 awarded to the winning helmsman in Handicap Series 4, sailed at Thorpe October to Year End.

2023 D. Tyrrell (Twinkle)
2022     S. Archer (Kelpie)
2021     No Race
2020     D. Tyrrell (Twinkle)
2019     G. Coulthard (Why Not)
2018     Mrs P. Woodcock (Whereabout)
2017     S. Woodcock (Kelpie)
2016     M. Lees (Wee Simby)
2014-15  S. Woodcock (Kelpie)

Originally awarded from 1979 to the winner of the Enterprise Class Races in the 3-Race day

 1979       N. Bowles (Stride)
1980-1    M. Gilburt (Ripper)
1982       D. Frary (Ripper)
1983       No Race
1984       D. Frary (Toccata)
1985-8    K. Edwards (Sundowner)
1989-93  No Race
1994       J. Reed (Not Again Dad)
1995       D. Goodwin (Carpe Diem)
1996-8    No Race
1999       Mrs P. Woodcock (Copii)
2000-01  No Race

Awarded from 2002 to the winner of the Enterprise/Wayfarer Races in the 3-Race Day

2002-04   R. Joy (Obsession)
2005-06   B. Woodcock (Copii)
2007        R. Joy (Obsession)
2008-13   Not awarded