Presented by the Hong Kong Flying Fifteen Association
Originally this Trophy was presented to the Fourth Classic Boat in the Regatta.
It was Re-Assigned in 2019 to Winner of the 10th Race in the World Championship
| Year | Sail No | Boat Name | Helm | Crew | Home Country |
| 2023 | 4105 | Best Foot Forward | N.Jerwood | B.Sheridan | AUS |
| 2019 | 3760 | GBR3760 | J.Davey | M.Huett | GBR |
| | | Trophy Re-Assigned - below winners were fourth in the Classic Fleet |
| 2015 | |
| 2013 | |
| 2011 | 2672 | Gazelle III | John Midolo | Gordon Cook | AUS |
| 2009 | 2672 | Gazelle III | Phil Lammonby | | AUS |
| 2007 | | | | | |
| 2005 | 485 | Gilmac | David Naylor | Terry Renner | GBR |
| 2003 | 2251 | | Ian Anderson | Richard Blaquerie | AUS |
| 2001 | 2841 | | Hemraj Gokal | Dennis Lapham | RSA |