Awarded to the mono-hull yacht with the Best Total Corrected Time in the Single Handed White Sail Divisions in the Two Day Youngstown Race.

Named for Jack Pitt of OHYC/OYC, a long time single handed racer and enthusiast.

2001	Gone with the Wind	Bill Eckersley, QCYC
2002	Epiphany	Ron Smallbone, PCYC
2003	Windriven	Jonathon Vinden, PCYC
2004	Windriven	Jonathon Vinden, PCYC
2005	Pelican Lee	Wendy McCloy, PCYC
2006	Windriven	Jonathon Vinden, PCYC
2007	Anne Bonny	John Ball, QCYC
2008	Windriven	Jonathon Vinden, PCYC
2009	Vague Location	Jim French, PCYC
2010	Mythos	Ted Spanos, PCYC
2011	North Caught	Wendy Northcotte, DYC