| Year | Owners | Boat_Name | Home_Port | Regatta_Location |
| 2024 | Bill & Colleen Wildner | Mr. Bill's Wild Ride | Harrison Twp. MI | North Star SC, MI |
| 2022 | Dean Fitzpatrick, Gary Snider | Honor Roll | Harrison Twp, MI | Annapolis YC, Annapolis, MD |
| 2018 | Bill & Colleen Wildner | Mr. Bill's Wild Ride | Harrison Twp. MI | North Star SC, Cheboygan MI |
| 2017 | Bill & Colleen Wildner | Mr. Bill's Wild Ride | Harrison Twp. MI | Annapolis YC, Annapolis, MD |
| 2014 | Bill & Colleen Wildner | Mr. Bill's Wild Ride | Harrison Twp. MI | Muskegon YC, Muskegon MI |
| 2012 | Ed Bayer, John Bayer, Jim Barnes | Falcon | Detroit Yacht Club | Erie YC, PA |
| 2011 | Ed Bayer, John Bayer, Jim Barnes | Falcon | Detroit Yacht Club | North Cape YC, MI |
| 2010 | Jim Sagerholm, Jerry Christofel | Aunt Jean | Annapolis, MD | Maryland |
| 2009 | Bill & Colleen Wildner | Mr. Bill's Wild Ride | Harrison Twp. MI | Muskegon |
| 2008 | Bill & Colleen Wildner | Mr. Bill's Wild Ride | Harrison Twp. MI | Detroit |
| 2007 | Bill & Colleen Wildner | Mr. Bill's Wild Ride | Harrison Twp. MI | Toronto |
| 2006 | Ed Bayer, John Bayer, Jim Barnes | Falcon | Detroit Yacht Club | Annapolis |
| 2005 | Mike Welch, Ed Bayer,John Bayer | Falcon | Detroit Yacht Club | Muskegon |
| 2004 | Dave Nickerson, Dana Seniff | Split Decision | Woodville, MA | Newport |
| 2003 | David Ogden | Buckaroo Banzai | Toronto, Ontario | Toronto |
| 2002 | John S Wimer | Fast Lane | Half Moon Bay, CA | San Francisco |
| 2001 | George Bergh | Cracker Jack | Grosse Point Farms, MI | Detroit |
| 2000 | Jim Sagerholm | Aunt Jean | Annapolis, MD | Newport |
| 1999 | Dave Nickerson, Dana Seniff | Split Decision | Woodville, MA | Annapolis |
| 1998 | Jim Kerr, John Spurrier | Melange | Seattle, WA | Seattle |
| 1997 | David Ogden | Buckaroo Banzai | Toronto, Ontario | Chicago |
| 1996 | David Champion | Choices III | Seattle, WA | Seattle |
| 1995 | Peter Duncan, Phil Lotz | Obstreperous | Darien, CT | Rye NY |
| 1994 | David Ogden | Buckaroo Banzai | Toronto, Ontario | 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 |
