| 1981 | | Ben Mondor, President, Pawtucket Red Sox |
| 1982 | | Joe Morgan, Manager, Pawtucket Red Sox |
| 1983 | | Dick Berardino, Manager, Elmira Suns |
| 1984 | | Mike Tamburo, President, Pawtucket Red Sox |
| 1985 | | Billy Jo Robidoux, Milwaukee Brewers |
| 1986 | | Pat Dobson, Pawtucket Red Sox |
| 1987 | | Sam Horn, Pawtucket Red Sox |
| 1988 | | Mickey Pina, Lynchburg Red Sox |
| 1989 | | Tim Naehring, Pawtucket Red Sox |
| 1990 | | Mo Vaughn, Pawtucket Red Sox
Phil Plantier, Pawtucket Red Sox |
| 1991 | | Rick Lancellotti, Pawtucket Red Sox |
| 1992 | | Ken Ryan, Pawtucket Red Sox |
| 1993 | | Paul Thoutsis, Pawtucket Red Sox |
| 1994 | | Eric Wedge, Pawtucket Red Sox |
| 1995 | | Mark Sweeney, St. Louis Cardinals |
| 1996 | | Buddy Bailey, Pawtucket Red Sox |
| 1997 | | Brian Rose, Pawtucket Red Sox |
| 1998 | | Trot Nixon, Pawtucket Red Sox |
| 1999 | | Wilton Veras, Pawtucket Red Sox |
| 2000 | | Carlos Pena, Texas Rangers |
| 2001 | | Greg Montalbano, Pawtucket Red Sox |
| 2002 | | Rocco Baldelli, Tampa Bay Devil Rays |
| 2003 | | Bronson Arroyo, Pawtucket Red Sox |
| 2004 | | Earl Snyder, Pawtucket Red Sox |
| 2005 | | Jon Lester, Pawtucket Red Sox |
| 2006 | | Jacoby Ellsbury, Portland Sea Dogs |
| 2007 | | Clay Buchholz, Portland Sea Dogs
Jacoby Ellsbury, Pawtucket Red Sox |
| 2008 | | Jeff Bailey, Pawtucket Red Sox |
| 2009 | | Casey Kelly, Greenville Drive/Salem Red Sox |
| 2010 | | Anthony Rizzo, Salem Red Sox/Portland Sea Dogs |
| 2011 | | Ryan Lavarnway, Portland Sea Dogs/Pawtucket Red Sox |
| 2012 | | Jackie Bradley, Jr., Salem Red Sox/Portland Sea Dogs |
