The Jan Santos Trophy was created by Antigua Sailing Week in 2001 in honour of Jan Santos for her dedicated service to Antigua Sailing Week over many many years. Following awarding of the trophy to Jan Santos in 2001, it has been awarded in subsequent years to honour individuals who have shown true dedication to the event over an extended period of time.
| Year | Winner |
|---|---|
| 2019 | Sean MacMillan |
| 2018 | Kathy Lammers |
| 2017 | Nicki Murphy |
| 2016 | Tony Maidment |
| 2015 | Hartmut Holtmann |
| 2014 | Geoffrey Pidduck |
| 2013 | Lyn Bardoe |
| 2012 | Pat Bailey |
| 2011 | Ann Morcam |
| 2010 | Tommy Patterson |
| 2009 | Arthur Wullschleger |
| 2008 | Hugh Bailey |
| 2007 | Jo Bowker |
| 2006 | Howard Hulford |
| 2005 | Peter Deeth |
| 2004 | Tom Hill |
| 2003 | Dougie Myers |
| 2002 | Jol Byerley |
| 2001 | Desmond & Lisa Nicholson |
