Presented in 1985 by former Commodore Wayland W. Rennie, this trophy, a framed print of John Barber's "Windward Start," shall be awarded annually to the FBYC enrolled yacht in the PHRF Spinnaker Class with the best score in the Offshore Division Fall Series. In 1995, the Board designated PHRF B as the class in which the trophy would be awarded. In 2023, after consultation with the presenter of this award, Wayland W. Rennie, the Board of Trustees designated PHRF non-Spin or Cruising Class as the award class for performance over the regular racing season. Changes in the criteria for awarding the Windward Start Trophy shall be by the determination of the Board of Trustees of Fishing Bay Yacht Club

The Windward Start Trophy shall be awarded to recognize the FBYC enrolled yacht in the PHRF non -Spinnaker Class or Cruising Class with the best score in the FBYC Offshore Division sponsored series events during the regular racing season. The selection of the recipient of this award shall be determined by the CBYRA High Point scoring formula.

1985		Triumph
1986		Wavelength
1987		Triumph
1988		Firebrand
1989		Albemarle Pippin
1990		Blizzard
1991		Albemarle Pippin
1992		Albemarle Pippin
1993		Stormking
1994		Triumph - A  Rappahannock - B
1995		Wavelength
1996		Wavelength
1997		Main Attraction
1998		Main Attraction
1999		Wavelength
2000		Wavelength
2001		Wavelength
2002		La Maga
2003		Night Music
2004		La Maga
2005		Shenanigan
2006		Nerid
2007		La Maga
2008		Elancer
2009		La Maga
2010		Nereid
2011		Elancer
2012		GOIN'
2013		Mad Hatter
2014		Mad Hatter
2015		Mad Hatter
2016		GOIN'
2017		Mad Hatter
2018		Mad Hatter
2019		Mad Hatter
2020		Mad Hatter
2021		Mad Hatter
2022		Mad Hatter
2023		Perseverance