Endeavour Trophy – Fleet Racing Winner
Presented by Peter Vincent
| Year | Skipper | Boat |
| 1998 | Ian Scott | Jim Dandy |
| 2000 | Laurie Wales | Thingy |
| 2001 | Mike Hefford | Jay Walker |
| 2002 | Peter Vincent | Endeavour |
| 2003 | Ian Scott | Sparkle |
| 2004 | Nigel Bates | Jim Dandy |
| 2005 | Graham Mander | Indulgence |
| 2006 | Graham Mander | Indulgence |
| 2007 | Leon Blewett | Aye Dunno |
| 2008 | Leon Blewett | Aye Dunno |
| 2009 | Leon Blewett | Aye Dunno |
| 2010 | Graham Mander | J75 Indulgence |
| 2011 | Leon Blewett | J211 White Plague |
| 2012 | Keith May | J16 Waiting for God |
| 2013 | Leon Blewett | J211 White Plague |
| 2014 | Graham Mander | J75 Indulgence |
| 2015 | Chris Koskela | J263 Nemesis |
| 2016 | David Hemsley | J95 |
| 2017 | Graeme Parratt | J277 |
| 2018 | Graeme Parratt | J277 |
| 2019 | Leon Blewett | J7 |
| 2020 | Graham Parratt | J277 |
| 2021 | Graham Parratt | J333 Tripple |
| 2022 | Graham Parratt | J333 Tripple |
| 2023 | Graham Parratt | J333 Tripple |
| 2024 | Graham Parratt | J333 Tripple |
| 2025 | Graham Parratt | J333 Tripple |