Shields half-model donated by Fleet #1 of Western Long Island Sound and the Larchmont Yacht Club in 1982 in memory of Cornelius Shields and awarded at the Shields National Championship Regatta to that skipper that achieves the greatest improvement in his standings from the previous Shields National Championship Regatta.
| Year | Award Winner | Winner's Fleet | Host Fleet |
|---|---|---|---|
| 2018 | Steve Mettler | Edgartown, MA | Edgartown, MA Edgartown Yacht Club |
| 2017 | Regatta abandoned due to Hurricane Jose | Mystic, CT Mason's Island Yacht Club | |
| 2016 | Pakhtun Shah | Monterey, CA | Monterey, CA Monterey Peninsula Yacht Club |
| 2015 | Eric Anderson | Monterey, CA | Newport, RI Ida Lewis Yacht Club |
| 2014 | Rolan Schultz | Larchmon, NY | W. Long Island Sound, NY Larchmont Yacht Club |
| 2013 | John Shannahan | Oxford, MD | Oxford, MD Tred Avon Yacht Club |
| 2012 | Shane Wells | Marion, MA | Marion, MA Beverly Yacht Club |
| 2011 | Bill Berry | Marion, MA | Oyster Bay, NY Seawanhaka Corinthian YC |
| 2010 | Richard Robbins Ethan Robbins | Marion, MA | Mystic, CT Mason's Island Yacht Club |
| 2009 | Peter Bailey | Oxford, MD | Chicago, IL Chicago Yacht Club |
| 2008 | Mike McCaffery Jan Slee | Newport, RI | Oxford, MD Tred Avon Yacht Club |
| 2007 | Jonathan Pope | Marion, MA | Newport, RI Ida Lewis Yacht Club |
| 2006 | John Burnham | Newport, RI | Buzzards Bay/Marion, MA Beverly Yacht Club |
| 2005 | W. Long Island Sound, NY Larchmont Yacht Club | ||
| 2004 | Charles Shoemaker | Newport, RI | Edgartown, MA Edgartown Yacht Club |
| 2003 | Robert E. Radway | Chicago, IL | Chicago, IL Chicago Yacht Club |
| 2002 | Roland Schulz | Larchmont, NY | Oyster Bay, NY Seawanhaka Corinthian YC |
| 2000 | W. Long Island Sound, NY Larchmont Yacht Club | ||
| 1999 | Bill Berry | Marion, MA | Buzzards Bay/Marion, MA Beverly Yacht Club |
| 1998 | Chicago, IL Chicago Yacht Club | ||
| 1997 | Narragansett Bay, RI | ||
| 1996 | Chris Cardoza | Larchmont, NY | Marblehead, MA |
| 1995 | Charles Levy | Newport, RI | W. Long Island Sound, NY Larchmont Yacht Club |
| 1994 | Bill Berry | Marion, MA | Marthas Vineyard, MA |
| 1993 | Dallas, TX | ||
| 1992 | Harold F. Skip McGuire | Larchmont, NY | Buzzards Bay/Marion, MA Beverly Yacht Club |
| 1991 | Bruce Muir | Newport, RI | Narragansett Bay, RI |
| 1990 | Rick Tears | Dallas, TX | Manhasset Bay, NY |
| 1989 | Jay Higgins | Chicago, IL | Chicago, IL |
| 1988 | Donald R. Tomlin | Larchmont, NY | Seawanhaka, NY |
| 1987 | David Crowley Bill Saltonstall | Marion, MA | Marthas Vineyard, MA |
| 1986 | David S. Cooke | Marblehead, MA | Buzzards Bay/Marion, MA Beverly Yacht Club |
| 1985 | Brian J. Ladouceur | Marion, MA | Northern Mass. Bay, MA |
| 1984 | James B. Moore Jr. | Manhasset Bay, NY | Monterey Bay, CA |
| 1983 | William Rich | Larchmont, NY | W. Long Island Sound, NY |