Named for early LTS instructor Todd Maybank, this trophy may be awarded to an LTS stdent or an instructor.  The trophy is presented to honour the silliest thing that happened at sailing school.

1974	Andy Coles/ David O’Neill
1975	John Miychele/ Dick Mitchele/ Ian Newport
1976	Bob Waldie/ Doug Maybank
1977	Jason Smith/ Joey Garvy
1978	No Record
1979	Silver Sail Program/ Paul “Flemboy” Fleming
1980	Shelagh Stonehan
1981	Jeff Bugbee/ Rob Thompson
1982	Daniel Bryk/ Daphane Humphreys
1983	Robyn Woolsey/ Timothy Gray
1984	David Larock/ The Instructors
1985	Doug Arrowsmith/ Kent Spraggett
1986	Diarmid Thompson/ Alex Lynch
1987	Timothy Chapchuk/ Lawrence Brooks
1988	Tanya Wharton/ Leeanne Sun Hing
1989	Rob Lytle/ Marcus Schwenzer
1990	Andrea Dienesch
1991	Phillip Rallon
1992	Kim Clancy/ Dave Caringi
1993	David El-Raheb/ John El-Raheb
1994-1997	No Record
1998	Graeme Lockett/ Justin Woodhouse
1999	Thomas Tielen
2000	Jonny Niblok
2000	Mitch Meyers
2001	Morgan Dakin
2002	Ron Philips
2003	Ron Philips
2004	Kyle Dakin
2005	No Record
2006	No Record
2007	Ian Middleton
2007	Sasha Spiteri
2008	Liam Tierney
2009	Michael Machado
2010	Not awarded
2013	Chris Burnes
2014	Jacob Long
2015	Alia Dennis