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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Sloppy Thurston | 152 | 1981-2000 | |
| 2 | Ted Gray | 138 | 1981-1997 | |
| 3 | Britt Burns | 130 | 1980-1997 | |
| 4 | Dave LaPoint | 121 | 1984-1993 | |
| 5 | Jim Maloney# | 117 | 1981-1998 | |
| 6 | Vern Kennedy | 114 | 1983-1994 | |
| 7 | Jeff Samardzija# | 112 | 1984-2000 | |
| 8 | Tyler Chatwood# | 111 | 1987-2000 | |
| 9 | Hank Aguirre | 109 | 1980-1991 | |
| 10 | Bob Knepper | 104 | 1980-1995 | |
| 11 | Steve Kraly | 102 | 1983-1995 | |
| 12 | Jesse Jefferson# | 101 | 1993-2000 | |
| 13 | Scott Kamieniecki# | 97 | 1991-2000 | |
| 14 | Dick Estelle# | 96 | 1985-1999 | |
| 15 | Thornton Lee# | 94 | 1991-2000 | |
| 15 | Brian Meadows | 94 | 1980-1990 | |
| 17 | Victor Santos | 92 | 1982-1994 | |
| 18 | Earl Wilson | 90 | 1980-1991 | |
| 19 | Jim Hughes# | 87 | 1993-2000 | |
| 20 | Rollie Sheldon | 86 | 1984-2000 | |
| 21 | Allan Ramirez | 85 | 1984-1995 | |
| 22 | Wade Miley# | 84 | 1988-2000 | |
| 22 | Walt Terrell# | 84 | 1983-2000 | |
| 24 | Bob Harris | 83 | 1991-1998 | |
| 25 | Francisco Barrios | 82 | 1980-1993 | |
| 26 | Chuck Dobson | 80 | 1987-1997 | |
| 26 | Dick Drott | 80 | 1983-1994 | |
| 28 | Les Cain | 79 | 1980-1996 | |
| 28 | Lynn Nelson | 79 | 1988-1994 | |
| 30 | Steve Johnson | 78 | 1980-1994 | |
| 30 | Steve Sundra | 78 | 1981-1991 | |
| 32 | Seth Etherton | 76 | 1992-1999 | |
| 32 | MacKenzie Gore# | 76 | 1993-2000 | |
| 34 | Fernando Arroyo | 74 | 1988-1997 | |
| 35 | Reese Olson | 73 | 1992-1998 | |
| 35 | Luke Walker | 73 | 1985-1995 | |
| 37 | Steven Brault | 72 | 1991-1998 | |
| 37 | Ben Sheets# | 72 | 1982-2000 | |
| 37 | Kohl Stewart | 72 | 1980-1988 | |
| 37 | Jim Unknown | 72 | 1980-1985 | |
| 37 | Al Williams | 72 | 1983-1992 | |
| 42 | Luis Leal# | 71 | 1994-2000 | |
| 42 | Yohan Pino | 71 | 1991-1997 | |
| 44 | Jim Unknown | 70 | 1980-1985 | |
| 44 | Charlie Wagner# | 70 | 1997-2000 | |
| 46 | Don August# | 69 | 1994-2000 | |
| 46 | Mike Boddicker | 69 | 1981-1989 | |
| 46 | Marv Breuer# | 69 | 1995-2000 | |
| 49 | Brian Givens# | 68 | 1992-1999 | |
| 49 | Robert Ray | 68 | 1981-1989 | |
| 51 | John Dettmer# | 67 | 1993-1999 | |
| 51 | Ramon Martinez | 67 | 1980-1992 | |
| 51 | Jim Peterson | 67 | 1986-1993 | |
| 51 | Sandy Vance# | 67 | 1993-2000 | |
| 55 | Gerry Arrigo | 66 | 1981-1998 | |
| 55 | Ralph Botting | 66 | 1988-1999 | |
| 55 | Bob Brown# | 66 | 1992-2000 | |
| 55 | Wayne Simpson | 66 | 1986-1998 | |
| 55 | Gary Wheelock | 66 | 1980-1991 | |
| 60 | Bill Butler | 65 | 1990-1999 | |
| 60 | Todd Stottlemyre | 65 | 1983-1999 | |
| 62 | Pete Charton | 64 | 1980-1987 | |
| 63 | Johnny Beazley | 63 | 1981-1993 | |
| 63 | Dave Eiland | 63 | 1984-1990 | |
| 63 | Shawn Estes | 63 | 1980-1990 | |
| 63 | Ken Kravec | 63 | 1981-1993 | |
| 67 | Marco Estrada# | 62 | 1994-2000 | |
| 67 | Ryan Rowland-Smith | 62 | 1986-1993 | |
| 67 | Jim Unknown | 62 | 1980-1985 | |
| 70 | John Burkett | 60 | 1984-1991 | |
| 70 | Jorge Campillo# | 60 | 1994-2000 | |
| 70 | Johan Oviedo# | 60 | 1993-2000 | |
| 73 | Dietrich Enns | 59 | 1983-1994 | |
| 73 | Livan Hernandez# | 59 | 1997-2000 | |
| 73 | Hector Noesi# | 59 | 1992-1997 | |
| 73 | Lefty Stewart# | 59 | 1991-2000 | |
| 73 | Jose Urena | 59 | 1981-1988 | |
| 73 | Chris Waters | 59 | 1986-1992 | |
| 79 | Barry Latman | 58 | 1988-1997 | |
| 79 | Calvin Maduro# | 58 | 1991-1999 | |
| 79 | Jack Russell | 58 | 1980-1990 | |
| 79 | Fred Sanford | 58 | 1986-1995 | |
| 79 | Jim Unknown | 58 | 1980-1985 | |
| 79 | Ismael Valdez | 58 | 1989-1995 | |
| 85 | Brandon Claussen# | 57 | 1993-2000 | |
| 85 | Brad Halsey# | 57 | 1992-1999 | |
| 85 | Mike LaCoss | 57 | 1988-1998 | |
| 85 | Paul LaPalme | 57 | 1985-1991 | |
| 85 | Antonio Osuna | 57 | 1987-1995 | |
| 85 | Jim Unknown | 57 | 1980-1989 | |
| 91 | Charlie Bishop | 56 | 1981-1990 | |
| 91 | Kyle Gibson# | 56 | 1995-1998 | |
| 91 | Shawn Hill | 56 | 1983-1997 | |
| 91 | Bob Moose | 56 | 1980-1993 | |
| 91 | Jim Unknown | 56 | 1980-1985 | |
| 96 | Todd Erdos | 55 | 1988-1995 | |
| 96 | Lil Stoner | 55 | 1990-1997 | |
| 96 | Jake Thompson | 55 | 1980-1989 | |
| 99 | Ron Kline# | 54 | 1992-1997 | |
| 99 | Dutch Leonard | 54 | 1981-1994 |
