| 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 |
| 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 |
| 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 |
History
