Spinnaker
Pursuit Spinnaker – Bradford Trophy
| Year | Yacht | Skipper | Club |
| 2019 | Dopodomani | Chris Zibailo | Constitution Yacht Club |
| 2018 | Sparkle Pony | Bill Finn/Francis Shiman-Hackett | Constitution/Savin Hill Yacht Clubs |
| 2017 | Sparkle Pony | Bill Finn/Francis Shiman-Hackett | Constitution/Savin Hill Yacht Clubs |
| 2016 | Wildthing | Dan Boyd & Mitch Wiest | Cottage Park Yacht Club |
| 2015 | Sparkle Pony | Bill Finn/Francis Shiman-Hackett | Constitution/Savin Hill Yacht Clubs |
| 2014 | Superstition | Chris Zibailo | Constitution Yacht Club |
| 2013 | Sparkle Pony | Bill Finn/Francis Shiman-Hackett | Constitution/Savin Hill Yacht Clubs |
| 2012 | Superstition | Steve Spangler & Chris Zibailo | Constitution Yacht Club |
| 2011 | Superstition | Steve Spangler & Chris Zibailo | Constitution Yacht Club |
| 2010 | Superstition | Steve Spangler & Chris Zibailo | Constitution Yacht Club |
| 2009 | Superstition | Steve Spangler & Chris Zibailo | Constitution Yacht Club |
| 2008 | Choucas | Jeffrey Talbot | Winthrop Yacht Club |
| 2007 | Akeepah | Jody Graul | Nahant Dory Club |
