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| Shields Fleet One 2002-2023 Results | |||||
| Season | Polly Ann Trophy | Most Improved | |||
| 2023 | Ward Young | Kurt Weisenfluh, Matt Tym | Greg Takata / Doug Campbell / Andrew Wertheim | ||
| 2022 | Ward Young | Kurt Weisenfluh | John Mawe | ||
| 2021 | Com Crocker | Com Crocker | Com Crocker | ||
| 2020 | Com Crocker | Com Crocker | Com Crocker | ||
| 2019 | Greg Takata / Doug Campbell / Andrew Wertheim | Greg Takata / Doug Campbell / Andrew Wertheim | Greg Takata / Doug Campbell / Andrew Wertheim | ||
| 2018 | Michael O'Connor / Com Crocker | Michael O'Connor / Com Crocker | Skip McGuire | ||
| 2017 | Frederick M Werblow | Frederick M Werblow | John Mawe | ||
| 2016 | Frederick M Werblow | Frederick M Werblow | Tim Sawyer / PJ O'Shea | ||
| 2015 | Frederick M Werblow | Frederick M Werblow | Pete McWhinnie/James Holland | ||
| 2014 | Com Crocker | Com Crocker | John Mawe | ||
| 2013 | Com Crocker | Com Crocker | Skip McGuire | ||
| 2012 | Frederick M Werblow | Frederick M Werblow | Greg Takata / Doug Campbell / Andrew Wertheim | ||
| 2011 | Com Crocker / Dual Macintyre | Com Crocker / Dual Macintyre | Skip McGuire | ||
| 2010 | Com Crocker / Dual Macintyre | Com Crocker / Dual Macintyre | Justin Gibbons / Phillips Johnston | ||
| 2009 | Com Crocker/ Dual Macintyre | Com Crocker / Dual Macintyre | John Mawe | ||
| 2008 | Com Crocker/ Kurt Weisenfluh | Com Crocker / Kurt Weisenfluh | Roland Schulz / Berenice & Alexandre deCirfontaine | ||
| 2007 | Com Crocker/ Kurt Weisenfluh | Com Crocker / Kurt Weisenfluh | Michael Carr | ||
| 2006 | Frederick M Werblow | Frederick M Werblow | Tim Sawyer | ||
| 2005 | Frederick M Werblow | Com Crocker / Kurt Weisenfluh | Justin Gibbons | ||
| 2004 | Michael Carr | Michael Carr | Greg Davis | ||
| 2003 | Michael Carr | H.L. DeVore | |||
| 2002 | Frederick M Werblow | Frederick M Werblow | |||
| 2001 | Frederick M Werblow | Frederick M Werblow | |||
| 2000 | Thierry de la Villehuchet / Joachim Shulz-Heik | Thierry de la Villehuchet / Joachim Shulz-Heik | |||
| 1999 | Thierry de la Villehuchet / Joachim Shulz-Heik | Thierry de la Villehuchet / Joachim Shulz-Heik | |||
| 1998 | Thierry de la Villehuchet / Joachim Shulz-Heik | Thierry de la Villehuchet / Joachim Shulz-Heik | |||
| 1997 | Thierry de la Villehuchet / Joachim Shulz-Heik | Thierry de la Villehuchet / Joachim Shulz-Heik | |||
| 1996 | Thierry de la Villehuchet / Joachim Shulz-Heik | Thierry de la Villehuchet / Joachim Shulz-Heik | |||
| 1995 | Thierry de la Villehuchet / Joachim Shulz-Heik | Thierry de la Villehuchet / Joachim Shulz-Heik | |||
| 1994 | Victor M. Onet, Jr. | ||||
| 1993 | Trevor Pardee (Sewanaka YC) | ||||
| 1992 | William Rich / Richard D. Ronnan | ||||
| 1991 | Victor M. Onet, Jr. | ||||
| 1990 | Richard D. Ronnan | ||||