Awarded to the mono-hull yacht with the Best Total Corrected Time in the Single-Handed While 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 | Jonathan Vinden, PCYC |
| 2004 | Windriven | Jonathan Vinden, PCYC |
| 2005 | Pelican Lee | Wendy McCloy, PCYC |
| 2006 | Windriven | Jonathan Vinden, PCYC |
| 2007 | Anne Bonny | John Ball, QCYC |
| 2008 | Windriven | Jonathan Vinden, PCYC |
| 2009 | Vague Location | Jim French, PCYC |
| 2010 | Mythos | Ted Spanos, PCYC |
| 2011 | North Caught | Wendy Northcotte, DYC |


Current
