Teams 
| Player | Year |
|---|---|
| Most Valuable Player | |
| Barry Bonds | 1992 |
| Barry Bonds | 1990 |
| Willie Stargell (Tie) | 1979 |
| Dave Parker | 1978 |
| Roberto Clemente | 1966 |
| Dick Groat | 1960 |
| Paul Waner | 1927 |
| Cy Young | |
| Doug Drabek | 1990 |
| Vernon Law | 1960 |
| Rookie of the Year | |
| Jason Bay | 2004 |
| Manager of the Year | |
| Jim Leyland | 1991 |
| Jim Leyland | 1990 |
| NLCS MVP | |
| Willie Stargell | 1979 |
| World Series MVP | |
| Willie Stargell | 1979 |
| Roberto Clemente | 1971 |
| Bill Mazeroski | 1960 |
| All-Star Game MVP | |
| Dave Parker | 1979 |
| Gold Gloves | |
| Nate McLouth (OF) | 2008 |
| Jose Lind (2B) | 1992 |
| Barry Bonds (OF) | 1992 |
| Andy Van Slyke (OF) | 1992 |
| Barry Bonds (OF) | 1991 |
| Andy Van Slyke (OF) | 1991 |
| Barry Bonds (OF) | 1990 |
| Andy Van Slyke (OF) | 1990 |
| Andy Van Slyke (OF) | 1989 |
| Andy Van Slyke (OF) | 1988 |
| Mike LaValliere (C) | 1987 |
| Tony Peña (C) | 1985 |
| Rick Reuschel (P) | 1985 |
| Tony Peña | 1984 |
| Tony Peña | 1983 |
| Dave Parker (OF) | 1979 |
| Dave Parker (OF) | 1978 |
| Dave Parker (OF) | 1977 |
| Roberto Clemente (OF) | 1972 |
| Roberto Clemente (OF) | 1971 |
| Roberto Clemente (OF) | 1970 |
| Roberto Clemente (OF) | 1969 |
| Roberto Clemente (OF) | 1968 |
| Roberto Clemente (OF) | 1967 |
| Bill Mazeroski (2B) | 1967 |
| Roberto Clemente (OF) | 1966 |
| Gene Alley (SS) | 1966 |
| Bill Mazeroski (2B) | 1966 |
| Roberto Clemente (OF) | 1965 |
| Bill Mazeroski (2B) | 1965 |
| Roberto Clemente (OF) | 1964 |
| Bill Mazeroski (2B) | 1964 |
| Roberto Clemente (OF) | 1963 |
| Bill Mazeroski (2B) | 1963 |
| Roberto Clemente (OF) | 1962 |
| Bill Virdon (OF) | 1962 |
| Roberto Clemente (OF) | 1961 |
| Bobby Shantz (P) | 1961 |
| Bill Mazeroski (2B) | 1961 |
| Bill Mazeroski (2B) | 1960 |
| Harvey Haddix (P) | 1960 |
| Harvey Haddix (P) | 1959 |
| Bill Mazeroski (2B) | 1959 |
| The Silver Slugger Award | |
| Jack Wilson (SS) | 2004 |
| Jay Bell (SS) | 1993 |
| Barry Bonds (OF) | 1990, 91, 92 |
| Andy Van Slyke (OF) | 1988, 92 |
| Bobby Bonilla (3B) | 1988, 90, 91 |
| Rick Rhoden (P) | 1984, 85, 86 |
| Johnny Ray (2B) | 1983 |
| Don Robinson (P) | 1982 |
| Pirates Roberto Clemente Award | |
| Neil Walker | 2010 |
| Andrew McCutchen | 2009 |
| Nate McLouth | 2008 |
| Freddy Sanchez | 2007 |
| Freddy Sanchez | 2006 |
| Jason Bay | 2005 |
| Jack Wilson | 2004 |
| Reggie Sanders | 2003 |
| Mike Williams | 2002 |
| Aramis Ramirez | 2001 |
| Brian Giles | 2000 |
| Brian Giles | 1999 |
| Jason Kendall | 1998 |
| Tony Womack, Kevin Young | 1997 |
| Jeff King | 1996 |
| Orlando Merced | 1995 |
| Dave Clark | 1994 |
| Jay Bell | 1993 |
| Andy Van Slyke | 1992 |
| Barry Bonds | 1991 |
| Doug Drabek | 1990 |
| Bill Landrum | 1989 |
| Andy Van Slyke | 1988 |
| Andy Van Slyke | 1987 |
| Johnny Ray | 1986 |
| Rick Reuschel | 1985 |
| Lee Lacy | 1984 |
| Tony Peña | 1983 |
| Jason Thompson | 1982 |
| Bill Madlock | 1981 |
| Mike Easler | 1980 |
| Willie Stargell | 1979 |
| Dave Parker | 1978 |
| Dave Parker | 1977 |
| Bill Robinson | 1976 |
| Dave Parker | 1975 |
| Al Oliver | 1974 |
| Willie Stargell | 1973 |
| Pirates Chuck Tanner Award | |
| Evan Meek | 2010 |
| Jack Wilson | 2009 |
| Jason Bay | 2008 |
| Adam LaRoche | 2007 |
| Jack Wilson | 2006 |
| The Fred Hutchison Award | |
| Sid Bream | 1990 |
| Rick Reuschel | 1985 |
| Don Robinson | 1984 |
| Willie Stargell | 1978 |
| The Sporting News NL MVP | |
| Arky Vaughn | 1935 |
| The Sporting News NL Player/Pitcher of the Year | |
| Barry Bonds | 1992 |
| Barry Bonds | 1991 |
| Doug Drabek | 1990 |
| Barry Bonds | 1990 |
| Andy Van Slyke | 1988 |
| Dave Parker | 1978 |
| Roberto Clemente | 1966 |
| Vernon Law | 1960 |
| Dick Groat | 1960 |
| Ralph Kiner | 1950 |
| The Sporting News NL Comeback Player of the Year | |
| Rick Reuschel | 1985 |
| Willie Stargell | 1978 |
| Vernon Law | 1965 |
| The Sporting News NL Fireman of the Year | |
| Dave Giusti | 1971 |
| Al McBean | 1964 |
| ElRoy Face | 1962 |
| The Sporting News Rookie Player of the Year | |
| Jason Kendall | 1996 |
| Johnny Ray | 1982 |
| The Sporting News Rookie Pitcher of the Year | |
| Tim Wakefield | 1992 |
| Mike Dunne | 1987 |
| Don Robinson | 1978 |
| The Sporting News Major League Executive of the Year | |
| Cam Bonifay | 1997 |
| Mike Dunne | 1987 |
| Don Robinson | 1978 |
| The Sporting News NL Manager of the Year | |
| Jim Leyland | 1992 |
| Jim Leyland | 1990 |
| Jim Leyland (Tie) | 1988 |
| Danny Murtaugh | 1970 |
| Danny Murtaugh | 1969 |
| Billy Meyer | 1948 |
| The Sporting News Major League Player of the Year | |
| Barry Bonds | 1990 |
| Willie Stargell | 1979 |
| Bill Mazeroski | 1960 |
| The Sporting News Major League Manager of the Year | |
| Danny Murtaugh | 1960 |
| The Sporting News Man of the Year | |
| Willie Stargell | 1979 |
