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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jacob Dover# | 101 | 2048-2060 | |
| 2 | Héctor López | 96 | 1985-1998 | |
| 3 | Jeremy Fritzinger# | 89 | 2049-2060 | |
| 4 | Gary Hampton | 72 | 2045-2058 | |
| 5 | Levi Marinaccio | 71 | 2045-2058 | |
| 6 | Dave Neira | 68 | 2023-2035 | |
| 7 | Brice Daniels | 67 | 2039-2057 | |
| 8 | Dave Michno | 64 | 1997-2007 | |
| 8 | Peyton Schwartz# | 64 | 2045-2057 | |
| 10 | Tommy Stipe# | 63 | 2048-2059 | |
| 11 | Frank Tucker | 62 | 1988-2002 | |
| 12 | Clarence Lyon | 60 | 1992-2010 | |
| 12 | Curt Webber# | 60 | 2044-2054 | |
| 14 | Tommy Fisher | 59 | 1993-2004 | |
| 14 | Pepe Sánchez | 59 | 1989-1996 | |
| 16 | Erik Crumb | 58 | 2027-2036 | |
| 16 | Anastasio López | 58 | 1986-1997 | |
| 18 | Nolan Hunter | 57 | 2047-2054 | |
| 18 | Sean Jenkins# | 57 | 2050-2058 | |
| 18 | Abdel McElwee# | 57 | 2052-2059 | |
| 21 | Dave Behymer | 56 | 2027-2037 | |
| 21 | Eros Cook | 56 | 1985-1998 | |
| 21 | Cris Morán | 56 | 1989-2001 | |
| 24 | Gene Ferguson | 55 | 1990-2000 | |
| 25 | Terry Gould | 54 | 1997-2006 | |
| 26 | Alexis Almeyda | 53 | 1995-2006 | |
| 26 | Jeremy Belcher | 53 | 2050-2054 | |
| 26 | Cody Lane# | 53 | 2049-2060 | |
| 26 | Tokuyuki Migita | 53 | 1994-2003 | |
| 26 | T.J. Millington | 53 | 2026-2034 | |
| 26 | Larent Nielson# | 53 | 2047-2060 | |
| 26 | Ed Steinbach | 53 | 2025-2039 | |
| 33 | Atticus Bowling | 51 | 2023-2036 | |
| 33 | Quenton Wagner# | 51 | 2054-2060 | |
| 35 | Jack Blandine# | 50 | 2052-2060 | |
| 35 | Joey Erickson | 50 | 2020-2029 | |
| 35 | Thomas Porter# | 50 | 2051-2060 | |
| 35 | Carter Schneider | 50 | 2041-2049 | |
| 39 | Dave Boyle | 49 | 2018-2024 | |
| 39 | Frank McCarthy | 49 | 2045-2051 | |
| 41 | Morgan Butler# | 48 | 2051-2060 | |
| 41 | Arturo Efugenio | 48 | 1981-1986 | |
| 41 | Reese Noble | 48 | 2045-2058 | |
| 41 | Tom Stahl | 48 | 2018-2026 | |
| 45 | Nate Bettis | 47 | 2024-2040 | |
| 45 | Tony Garrett | 47 | 2026-2039 | |
| 45 | Jack Lewis | 47 | 1981-1989 | |
| 45 | Bradley Nagle# | 47 | 2054-2059 | |
| 45 | Adelaide Sarafana | 47 | 1993-2003 | |
| 50 | Samuel Holroyd# | 46 | 2047-2056 | |
| 50 | Jordan Vidal | 46 | 2001-2010 | |
| 52 | Arlon Chabwera# | 45 | 2046-2060 | |
| 52 | Sean Drury | 45 | 2044-2055 | |
| 52 | Nazir Liddell | 45 | 2030-2038 | |
| 52 | Adam McCall | 45 | 2042-2054 | |
| 56 | Oscar Archuletta | 44 | 2000-2012 | |
| 56 | Jamie Galler | 44 | 2009-2016 | |
| 56 | Pat Hall | 44 | 2012-2017 | |
| 56 | Joseph Starnes# | 44 | 2050-2060 | |
| 56 | Brennan Wright# | 44 | 2050-2057 | |
| 61 | Eugene Brown# | 43 | 2048-2060 | |
| 61 | A.J. Clauss | 43 | 2016-2025 | |
| 61 | Brandyn Garcia | 43 | 2035-2045 | |
| 61 | Casey Luder# | 43 | 2046-2054 | |
| 61 | Ed Phillipps | 43 | 2027-2038 | |
| 61 | Guillermo Quritones | 43 | 1978-1981 | |
| 67 | Ricky Alvarez | 42 | 2000-2015 | |
| 67 | Dave Crumb | 42 | 2008-2021 | |
| 67 | Evan Hale# | 42 | 2052-2060 | |
| 67 | Griffin Heustis | 42 | 2046-2058 | |
| 67 | Pat Mickiewicz | 42 | 2022-2034 | |
| 67 | Dex Nelson | 42 | 2027-2035 | |
| 67 | Grant Walker# | 42 | 2046-2060 | |
| 74 | Zack Alexander | 41 | 2003-2016 | |
| 74 | Casey Barber# | 41 | 2056-2060 | |
| 74 | Paul Caragiale | 41 | 2036-2043 | |
| 74 | Willie Cruz | 41 | 1992-2001 | |
| 74 | Pat Fahey | 41 | 2027-2041 | |
| 74 | Javier Garcia | 41 | 1994-2005 | |
| 74 | Kong Li | 41 | 2005-2017 | |
| 74 | Tarin Ma# | 41 | 2055-2060 | |
| 74 | Preston Parnell# | 41 | 2050-2060 | |
| 74 | Joe Poso | 41 | 1978-1986 | |
| 74 | J.J. Ray | 41 | 2022-2037 | |
| 74 | Shotaro Tada | 41 | 1985-1993 | |
| 86 | Manny Aguilar | 40 | 1991-2002 | |
| 86 | Tanner Bangle | 40 | 1996-2007 | |
| 86 | Gary Boivin | 40 | 1981-1996 | |
| 86 | Frisco Cuellar | 40 | 1996-2006 | |
| 86 | Jayden Eicher | 40 | 2026-2034 | |
| 86 | Alphonse Lamaalem# | 40 | 2054-2060 | |
| 86 | D.J. Matern | 40 | 2023-2033 | |
| 86 | Tom Meadows | 40 | 2016-2020 | |
| 86 | Manny Medina | 40 | 1996-2005 | |
| 86 | Jamie Ohmer | 40 | 2003-2009 | |
| 86 | Wiley Pakenham | 40 | 1983-1988 | |
| 86 | Lyndon Williams | 40 | 1991-2001 | |
| 86 | Héctor Ybarra | 40 | 1990-1998 | |
| 99 | Tom Cannon | 39 | 2017-2021 | |
| 99 | Samuel Carruthers | 39 | 2039-2045 |
