The Robert Jensen Masters Trophy is awarded annually to the highest placing skipper over sixty years of age that has not also been awarded either the Novice, Travel or Don Quixote at the current regatta.
| Year | Winner |
|---|---|
| 2022 | John Walter |
| 2021 | Steve Clancy |
| 2020 | Not Held / COVID |
| 2019 | Jim Taylor |
| 2018 | Rick McGregor |
| 2017 | Seamus Hourihan |
| 2016 | Bob Bernstein |
| 2015 | Seamus Hourihan |
| 2014 | Jim Taylor |
| 2013 | Bob Bernstein |
| 2012 | Dick Hitchcock |
| 2011 | Bob Bernstein |
| 2010 | Doug Trees |
| 2009 | Doug Trees |
| 2008 | Doug Trees |
| 2007 | Doug Trees |
| 2006 | Robert Jensen |