| Year | Team Name | League | Division | Affilate | W | L | Pct | Rank | Managers | Stadium | Playoffs | |
| 2013 | GCL Pirates | - | GCL | North | PIT | 0 | 0 | -- | 0 | Milver Reyes | Pirate City Stadium | dnq |
| 2012 | GCL Pirates | - | GCL | North | PIT | 36 | 24 | .600 | 2 | Tom Prince | Pirate City Stadium | League Champions |
| 2011 | GCL Pirates | - | GCL | North | PIT | 34 | 26 | .567 | 2 | Pirate City Stadium | Lost in Semi-Finals | |
| 2010 | GCL Pirates | - | GCL | North | PIT | 29 | 30 | .492 | 4 | Tom Prince | Pirate City Stadium | dnq |
| 2009 | GCL Pirates | - | GCL | North | PIT | 29 | 31 | .483 | 4 | Tom Prince | Pirate City Stadium | dnq |
| 2008 | GCL Pirates | GCL | South | PIT | 37 | 19 | .661 | 1 | Tom Prince | Pirate City Stadium | Lost in Semi-Finals | |
| 2007 | GCL Pirates | GCL | Southern | PIT | 26 | 30 | .464 | 4 | Tom Prince | Pirate City Stadium | dnq | |
| 2006 | GCL Pirates | GCL | North | PIT | 27 | 26 | .509 | 3 | Turner Ward | Pirate City Stadium | dnq | |
| 2005 | GCL Pirates | GCL | Southern | PIT | 28 | 26 | .519 | 2 | Jeff Livesey | Pirate City Stadium | dnq | |
| 2004 | GCL Pirates | GCL | Southern | PIT | 30 | 28 | .517 | 3 | Woody Huyke | Pirate City Stadium | dnq | |
| 2003 | GCL Pirates | GCL | Northern | PIT | 36 | 20 | .643 | 1 | Woody Huyke | Pirate City Stadium | Lost in Finals | |
| 2002 | GCL Pirates | GCL | Southern | PIT | 37 | 23 | .617 | 1 | Woody Huyke | Pirate City Stadium | Lost in Semi-Finals | |
| 2001 | GCL Pirates | GCL | Western | PIT | 22 | 34 | .393 | 6 | Woody Huyke | Pirate City Stadium | dnq | |
| 2000 | GCL Pirates | GCL | Northern | PIT | 34 | 26 | .567 | 2 | Woody Huyke | Pirate City Stadium | dnq | |
| 1999 | GCL Pirates | GCL | Western | PIT | 24 | 35 | .407 | 5 | Woody Huyke | Pirate City Stadium | dnq | |
| 1998 | GCL Pirates | GCL | Western | PIT | 25 | 35 | .417 | 6 | Woody Huyke | Pirate City Stadium | dnq | |
| 1997 | GCL Pirates | GCL | Northwest | PIT | 27 | 32 | .458 | 6 | Woody Huyke | Pirate City Stadium | dnq | |
| 1996 | GCL Pirates | GCL | Northwest | PIT | 28 | 31 | .475 | 3 | Woody Huyke | Pirate City Stadium | dnq | |
| 1995 | GCL Pirates | GCL | Northwest | PIT | 23 | 36 | .390 | 4 | Woody Huyke | Pirate City Stadium | dnq | |
| 1994 | GCL Pirates | GCL | Western | PIT | 25 | 35 | .417 | 4 | Woody Huyke | Pirate City Stadium | dnq | |
| 1993 | GCL Pirates | GCL | Western | PIT | 21 | 38 | .356 | 7 | Woody Huyke | Pirate City Stadium | dnq | |
| 1992 | GCL Pirates | GCL | Central | PIT | 23 | 37 | .383 | 4 | Woody Huyke | Pirate City Stadium | dnq | |
| 1991 | GCL Pirates | GCL | Central | PIT | 30 | 29 | .508 | 3 | Woody Huyke | Pirate City Stadium | dnq | |
| 1990 | GCL Pirates | GCL | South | PIT | 25 | 37 | .403 | 7 | Pirate City Stadium | dnq | ||
| 1989 | GCL Pirates | GCL | Southern | PIT | 21 | 42 | .333 | 8 | Woody Huyke | Pirate City Stadium | dnq | |
| 1988 | GCL Pirates | GCL | Southern | PIT | 26 | 37 | .413 | 5 | Julio Garcia | Pirate City Stadium | dnq | |
| 1987 | GCL Pirates | GCL | Northern | PIT | 33 | 30 | .524 | 2 | Woody Huyke | Pirate City Stadium | dnq | |
| 1986 | GCL Pirates | GCL | Northern | PIT | 24 | 39 | .381 | 5 | Woody Huyke | Pirate City Stadium | dnq | |
| 1985 | GCL Pirates | GCL | Northern | PIT | 15 | 47 | .242 | 5 | Woody Huyke | Pirate City Stadium | dnq | |
| 1984 | GCL Pirates | GCL | Northern | PIT | 21 | 42 | .333 | 5 | Woody Huyke | Pirate City Stadium | dnq | |
| 1983 | GCL Pirates | GCL | Northern | PIT | 28 | 32 | .467 | 3 | Woody Huyke | Pirate City Stadium | dnq | |
| 1982 | GCL Pirates | GCL | - | PIT | 27 | 35 | .435 | 9 | Woody Huyke | Pirate City Stadium | dnq | |
| 1981 | GCL Pirates | GCL | - | PIT | 32 | 28 | .533 | 5 | Woody Huyke | Pirate City Stadium | dnq | |
| 1980 | GCL Pirates | GCL | - | PIT | 24 | 39 | .381 | 8 | Woody Huyke | Pirate City Stadium | dnq | |
| 1979 | GCL Pirates | GCL | - | PIT | 20 | 32 | .385 | 6 | Woody Huyke | Pirate City Stadium | dnq | |
| 1978 | GCL Pirates | GCL | - | PIT | 21 | 32 | .396 | 6 | Woody Huyke | Pirate City Stadium | dnq | |
| 1977 | GCL Pirates | - | GCL | - | PIT | 22 | 32 | .407 | 7 | dnq | ||