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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Omar Green | 23 | 2056-2059 | |
| 2 | Brian Jordan | 22 | 2065-2067 | |
| 3 | Jesus Nistal | 21 | 2076-2079 | |
| 4 | Tony Tafoya | 19 | 2053-2059 | |
| 5 | Matt Tucker# | 18 | 2094-2096 | |
| 6 | Nick Bodkin | 17 | 2072-2074 | |
| 6 | Stephen Straka# | 17 | 2079-2081 | |
| 6 | Nathaniel Valmont# | 17 | 2093-2096 | |
| 9 | Tom Brinkmeyer | 16 | 2053-2054 | |
| 9 | Ramon Delgado | 16 | 2053-2056 | |
| 9 | DeAndre Hart | 16 | 2032-2034 | |
| 9 | Matt Manning | 16 | 2016-2018 | |
| 9 | Corey Myers | 16 | 2045-2047 | |
| 9 | Edwin Sanchez | 16 | 2050-2052 | |
| 9 | Josh Stache | 16 | 2050-2052 | |
| 16 | Jon Bradley | 15 | 2058-2059 | |
| 16 | Brandon Davis | 15 | 2037-2041 | |
| 16 | Ricky Dominguez | 15 | 2072-2074 | |
| 16 | Jim Gamblin# | 15 | 2095-2097 | |
| 16 | Eric Parks | 15 | 2078-2079 | |
| 16 | Chris Rutherford# | 15 | 2095-2098 | |
| 16 | Seth Tull | 15 | 2048-2049 | |
| 16 | Mike Verret | 15 | 2077-2079 | |
| 24 | Paul Caylor# | 14 | 2094-2096 | |
| 24 | Chris Colon | 14 | 2056-2058 | |
| 24 | Jaime Davis | 14 | 2026-2028 | |
| 24 | Casey Giardino | 14 | 2033-2035 | |
| 24 | Brian Hodge | 14 | 2078-2080 | |
| 24 | Tom Koehl | 14 | 2052-2053 | |
| 24 | Eric Lewis# | 14 | 2087-2090 | |
| 24 | Alberto Sandoval# | 14 | 2094-2098 | |
| 24 | Brian Williams# | 14 | 2087-2089 | |
| 33 | Malachi Banks# | 13 | 2090-2094 | |
| 33 | Kyle Barr# | 13 | 2088-2090 | |
| 33 | Ben Clemons | 13 | 2079-2081 | |
| 33 | Mark Cook | 13 | 2045-2048 | |
| 33 | Jeremy Kisler | 13 | 2049-2050 | |
| 33 | Chris Leeder# | 13 | 2094-2097 | |
| 33 | Juan Maldonado | 13 | 2063-2064 | |
| 33 | Alex Ortiz | 13 | 2050-2053 | |
| 33 | Danny Ozuna# | 13 | 2096-2098 | |
| 33 | John Ringler | 13 | 2049-2052 | |
| 33 | Jaden Seals# | 13 | 2090-2092 | |
| 33 | Jim Shea | 13 | 2024-2026 | |
| 33 | Brad Stoves# | 13 | 2087-2089 | |
| 33 | Greg Taylor# | 13 | 2090-2094 | |
| 47 | Mike Bartley# | 12 | 2084-2086 | |
| 47 | John Erchul | 12 | 2058-2061 | |
| 47 | Jeremy Estevez | 12 | 2077-2078 | |
| 47 | Jose Flores | 12 | 2062-2063 | |
| 47 | Alex Hernandez# | 12 | 2094-2098 | |
| 47 | Matt Hommes# | 12 | 2080-2082 | |
| 47 | Danny Hunter | 12 | 2051-2054 | |
| 47 | Kevin Ingram | 12 | 2051-2052 | |
| 47 | Marcello Jarvis# | 12 | 2094-2096 | |
| 47 | Justin LaPuma | 12 | 2039-2041 | |
| 47 | Zachery Linker | 12 | 2079-2081 | |
| 47 | Tim Mabe | 12 | 2052-2054 | |
| 47 | Angelo Medina | 12 | 2053-2054 | |
| 47 | Bill Molina | 12 | 2020-2021 | |
| 47 | Matt O'Bryan# | 12 | 2095-2096 | |
| 47 | Jesus Ramos# | 12 | 2089-2090 | |
| 47 | Bill Rockhold | 12 | 2048-2049 | |
| 47 | Enrique Rodriguez | 12 | 2053-2055 | |
| 47 | Shane Schmalz# | 12 | 2086-2088 | |
| 47 | Bill Swanson | 12 | 2026-2028 | |
| 47 | Mike Wallace# | 12 | 2094-2096 | |
| 47 | Andy Wilkosz | 12 | 2031-2033 | |
| 69 | Tony Barrera | 11 | 2040-2042 | |
| 69 | Pablo Castaneda# | 11 | 2095-2097 | |
| 69 | Dylan Colucci | 11 | 2022-2023 | |
| 69 | Sal Cuellar# | 11 | 2093-2094 | |
| 69 | John Dougherty | 11 | 2057-2058 | |
| 69 | Matt Edinger# | 11 | 2082-2084 | |
| 69 | Tommy Elson | 11 | 2026-2026 | |
| 69 | Ryan Feierabend | 11 | 2003-2008 | |
| 69 | Steve Frenn# | 11 | 2095-2096 | |
| 69 | Rodrigo Gonzales# | 11 | 2090-2092 | |
| 69 | Tristan Graham | 11 | 2035-2037 | |
| 69 | Ezequiel Guerrero# | 11 | 2094-2095 | |
| 69 | Norge Carlos Hernandez# | 11 | 2084-2087 | |
| 69 | Brad Ibarra | 11 | 2056-2059 | |
| 69 | T.J. Johnson# | 11 | 2092-2093 | |
| 69 | Andy Lundgren | 11 | 2068-2069 | |
| 69 | Pat Lynn | 11 | 2053-2054 | |
| 69 | Joe Nelson | 11 | 2058-2061 | |
| 69 | Seth Oltmans# | 11 | 2091-2093 | |
| 69 | Enrique Pera | 11 | 2022-2023 | |
| 69 | Mike Rios | 11 | 2038-2043 | |
| 69 | Eddie Rivera# | 11 | 2082-2084 | |
| 69 | Willie Rivera | 11 | 2059-2061 | |
| 69 | Danny Roldan | 11 | 2068-2071 | |
| 69 | Johnny Salinas | 11 | 2027-2029 | |
| 69 | Ricky Sandoval# | 11 | 2093-2097 | |
| 69 | Andy Sutton | 11 | 2065-2067 | |
| 69 | Jose Vargas# | 11 | 2091-2095 | |
| 97 | Ricky Arbelaez# | 10 | 2083-2084 | |
| 97 | Ryan Bennett# | 10 | 2091-2093 | |
| 97 | Jim Brennan# | 10 | 2088-2089 | |
| 97 | Tristen Campbell# | 10 | 2090-2091 |
