| | Year | Owners | Boat Name | Location/Home Port | Regatta Location |
|
| 2009 | Bill & Colleen Wildner | Mr. Bill's Wild Ride | Harrison Twp, MI | In Muskegon |
|
| 2008 | Bill & Colleen Wildner | Mr. Bill's Wild Ride | Harrison Twp, MI | In Detroit |
|
| 2007 | Bill & Colleen Wildner | Mr. Bill's Wild Ride | Harrison Twp, MI | In Toronto |
|
| 2006 | Mike Welch, Ed Beyer,
John Beyer | Falcon | Grosse Point Farms, MI | In Annapolis |
|
| 2005 | Mike Welch, Ed Beyer,
John Beyer | Falcon | Grosse Point Farms, MI | In Muskegon |
|
| 2004 | Dave Nickerson, Dana Seniff | Split Decision | Woodville, MA | In Newport |
|
| 2003 | David Ogden | Buckaroo Banzai | Toronto, Ontario | In Toronto |
|
| 2002 | John S Wimer | Fast Lane | Half Moon Bay, CA | In San Francisco |
|
| 2001 | George Bergh | Cracker Jack | Grosse Point Farms, MI | In Detroit |
|
| 2000 | Jim Sagerholm | Aunt Jean | Annapolis, MD | In Newport |
|
| 1999 | Dave Nickerson, Dana Seniff | Split Decision | Woodville, MA | In Annapolis |
|
| 1998 | Jim Kerr, John Spurrier | Melange | Seattle, WA | In Seattle |
|
| 1997 | David Ogden | Buckaroo Banzai | Toronto, Ontario | In Chicago |
|
| 1996 | David Champion | Choices III | Seattle, WA | In Seattle |
|
| 1995 | Peter Duncan, Phil Lotz | Obstreperous | Darien, CT | In Rye NY |
|
| 1994 | David Ogden | Buckaroo Banzai | Toronto, Ontario | In Toronto |
|
| 1993 | Don Trask | Raptor | San Francisco, CA | |
|
| 1992 | Jeff Todd | Hot Toddy | Annapolis, MD | |
|
| 1991 | Jeff Udell | Telegraph Road | Riverside, NJ | |
|
| 1990 | Bruce MacLeod | Skye Hie | Rye, NY | |
|
| 1989 | Bill Selzenoff | Tatiana | Long Beach, CA | |
|
| 1988 | Will Keyworth | Moonbeam | Annapolis, MD | |
|
| 1987 | Randy Pittman | Juggernaut | Seattle, WA | |
|
| 1986 | Paul Fleming | Hot Entrée | Portland, ME | |
|
| 1985 | Wiley Wakeman | Ripcord | Portland, ME | |
|
| 1984 | Rick Howard | Smoke | Houston, TX | |
|