The first place Skipper and Crew retain possession of the coveted Cocktail Shaker for a year and use the official Lake Placid Regatta sail in the following year’s race.
| PAST WINNERS | |
| 2017 | Whitney Smith & Johnny Shaw |
| 2016 | Ben Kasper & Sandra Reiss |
| 2015 | Thomas A. Wey Jr. & Gunnar Wey |
| 2014 | Emily Miller & Andy Rochat |
| 2013 | Fred & Hayley Jubitz |
| 2012 | Peg & Bell Jackson |
| 2011 | Greg Reiss & Heidi Reiss |
| 2010 | Kirsten & Michael Dunleavy |
| 2009 | Rob & Mimi Ughetta |
| 2008 | Thomas A. Wey Jr. & Emily Miller |
| 2007 | Thomas A. Wey Jr. & Emily Miller |
| 2006 | Gary Corwin & Rosie Corwin |
| 2005 | Henry Bonner & Marnie Bonner |
| 2004 | John Rosenthal & Nancy Rosenthal |
| 2003 | Fred Jubitz & Taylor Jubitz |
| 2002 | Ed Gardner & Abby Evans |
| 2001 | Bill Ughetta & George Ughetta |
| 2000 | Ed Gardner & Peter Cutler |
| 1999 | Roger Smith & Juliana Smith |
| 1998 | Bruce McLean & R.J. Lavalle |
| 1997 | Mark Ughetta & Max Haspel |
| 1996 | Laura Anthony & Missy Geisler |
| 1995 | Julia Battel & Mark Tutell |
| 1994 | Jim Vaughn & Betsy Hlavacek |
| 1993 | Merritt Ashmead & Tim Robinson |
| 1992 | Merritt Ashmead & Tim Robinson |
| 1991 | Howard Love & David Vaughn |
| 1990 | Chris Wurster & Jamey Rhoades |
| 1989 | J.D.Reynolds & Steven Reynolds |
| 1988 | Sara Ris & Buddy Ris |
| 1987 | Mo Distin & Mili Distin |
| 1986 | Chris Wurster & Fraser Horn |
| 1985 | Mo Distin & Mili Distin |
| 1984 | David McCary & Tina McCary |
| 1983 | Margot Doering & Burt Stewart |
| 1982 | Gregg Reiss & Jim McNamara |
| 1981 | Mark Wilson & Kim Wilson |
| 1980 | John Rosenthal & Nancy Rosenthal |
| 1979 | Doug Stewart & Bert Stewart |
| 1978 | Bud Ris & Kate Thompson |
| 1977 | Dan Donaldson & Cathy Osterlano |
| 1976 | Ted Perry & Charles Wemyss |
| 1975 | Ted Perry & Lorna Perry |
| 1974 | Ted Perry & Lorna Perry |
| 1973 | N. Collamer & Charles Wemyss |
| 1972 | Naj Wikoff & Dan Luce |
| 1971 | Bill Edgerton & Susan Wemyss |