The Charles S. Roberts awards are presented at the World Boardgaming Championships (July/August) since 2000. Before that they were presented at Origins (July) and until 1987 a part of the Origins Awards.
James F. Dunnigan Award
James F. Dunnigan Award
2008 Uwe Eickert
2007 Dean Essig
2006 Tetsuya Nakamura & Adam Starkweather
2005 Ananda Gupta & Jason Matthews
2004 Lee Brimmicombe Wood
2003 Rick Young & Jesse Evans
2002 Ben Hull
2001 Volko Ruhnke
2000 Mark Simonitch
1999 Ted Raicer
1998 Mark Herman
1997 Dean Essig
1996 Ty Bomba
1995 Ted Raicer
1994 Dean Essig
1993 Dean Essig
1992 Ben Knight
1991 Mark Simonitch & EastFront
1990 Don Greenwood
1989 Modern Naval Battles
More info: here, here and here.
2007 Dean Essig
2006 Tetsuya Nakamura & Adam Starkweather
2005 Ananda Gupta & Jason Matthews
2004 Lee Brimmicombe Wood
2003 Rick Young & Jesse Evans
2002 Ben Hull
2001 Volko Ruhnke
2000 Mark Simonitch
1999 Ted Raicer
1998 Mark Herman
1997 Dean Essig
1996 Ty Bomba
1995 Ted Raicer
1994 Dean Essig
1993 Dean Essig
1992 Ben Knight
1991 Mark Simonitch & EastFront
1990 Don Greenwood
1989 Modern Naval Battles
More info: here, here and here.