The Upware Boat Club was founded in November 1985 by Sid Fisher and Maureen Taylor.
| Year | Commodore | Boat |
| 1986 | Sid Fisher | Mon Ami |
| 1987 | Colin Lennox | Sachamanda |
| 1988 | Keith Dickinson | Addicted |
| 1989 | Keith Dickinson | Addicted |
| 1990 | Bernard Drage | Harnser |
| 1991 | Bob Sage | Sandbee |
| 1992 | Peggy Drage | Rhapsody |
| 1993 | Peggy Drage | Rhapsody |
| 1994 | Bob Wells | Foxy Lady |
| 1995 | Peter Owen | Great Expectations |
| 1996 | Peter Owen | Great Expectations |
| 1997 | John Dodsworth | Princess Elaine |
| 1998 | John Dodsworth | Princess Elaine |
| 1999 | Bob Wells | Merlin |
| 2000 | Tim Mountain | Harpagon |
| 2001 | Tim Mountain | Harpagon |
| 2002 | Philip Baker | Aquila |
| 2003 | Philip Baker | Aquila |
| 2004 | Gary Hartwig | Liziana |
| 2005 | Gary Hartwig | Liziana |
| 2006 | Roly Griffen | Sovereign |
| 2007 | Roly Griffen | Sovereign |
| 2008 | John Walsh | WKD |
| 2009 | Mike Sheppard | Topaz |
| 2010 | Mike Sheppard | Topaz |
| 2011 | Terry Read | Sayonara |
| 2012 | Terry Read | Sayonara |
| 2013 | Ken Pryor | Black Orchid |
| 2014 | Ken Pryor | Black Orchid |
| 2015 | Ken Pryor | Black Orchid |
| 2016 | Chris Bottley | Just For Play |
| 2017 | Chris Bottley | Just For Play |
| 2018 | Jane Read | Valdaroma |
| 2019 | Jane Read | Valdaroma |
| 2020 | Steve Crosson Smith | Apres Ski |
| 2021 | Steve Crosson Smith | Apres Ski |
| 2022 | Steve Crosson Smith | Apres Ski |
| 2023 | David Harris | Threepenny |