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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Roberto Arceo* | 20 | 2033-2049 | |
| 1 | Mario Segura* | 20 | 2060-2080 | |
| 3 | Matt Gilman* | 19 | 2051-2071 | |
| 4 | Noel Murch* | 16 | 2039-2057 | |
| 5 | Manny Cruz* | 15 | 2027-2043 | |
| 5 | Josh Lowe | 15 | 2033-2047 | |
| 5 | Javier Venzor* | 15 | 2022-2041 | |
| 8 | Fred Cloninger* | 14 | 2033-2044 | |
| 8 | Bob Johannes | 14 | 2080-2096 | |
| 8 | Jeremy LeVan | 14 | 2053-2064 | |
| 8 | Max Reyes* | 14 | 2031-2046 | |
| 8 | Ricardo Rivera | 14 | 2023-2044 | |
| 8 | Hugo Vega | 14 | 2072-2088 | |
| 8 | Matt Whisler* | 14 | 2042-2056 | |
| 15 | Max Fried* | 13 | 2017-2030 | |
| 15 | Corey Winer | 13 | 2075-2088 | |
| 17 | Alastair Colson | 12 | 2074-2091 | |
| 17 | Javier Covarrubias* | 12 | 2061-2077 | |
| 17 | Steve Jardon | 12 | 2077-2091 | |
| 17 | Logan Lowe* | 12 | 2062-2079 | |
| 17 | Jose Rubio* | 12 | 2060-2079 | |
| 22 | Manny Baez | 11 | 2069-2083 | |
| 22 | Jose Benitez# | 11 | 2087-2098 | |
| 22 | Brian Casey* | 11 | 2048-2061 | |
| 22 | Jon Meger# | 11 | 2082-2098 | |
| 22 | Seth Stowers | 11 | 2027-2043 | |
| 22 | Roberto Villarreal | 11 | 2062-2074 | |
| 28 | Erik Brasier | 10 | 2038-2054 | |
| 28 | Jimmy Crowden | 10 | 2024-2033 | |
| 28 | Justin Pagel | 10 | 2081-2096 | |
| 28 | Dave Upton | 10 | 2062-2075 | |
| 28 | Roberto Vidana | 10 | 2024-2037 | |
| 33 | Armando Almodovar* | 9 | 2020-2035 | |
| 33 | Devin Carl* | 9 | 2026-2043 | |
| 33 | Steve Coutts | 9 | 2077-2094 | |
| 33 | Chris Flores | 9 | 2060-2071 | |
| 33 | Jose Garza | 9 | 2027-2037 | |
| 33 | Nate Howe | 9 | 2063-2077 | |
| 33 | Braxton Janke | 9 | 2046-2060 | |
| 33 | Andy Mediate | 9 | 2070-2088 | |
| 33 | Adonis Medina | 9 | 2019-2035 | |
| 33 | Dave Quintana | 9 | 2023-2040 | |
| 33 | Chris Sable# | 9 | 2091-2098 | |
| 33 | Bobby Tapia | 9 | 2082-2097 | |
| 45 | David Amaya | 8 | 2055-2073 | |
| 45 | Alex Batista* | 8 | 2058-2073 | |
| 45 | Victor Cevallos | 8 | 2067-2083 | |
| 45 | Brian Clouse | 8 | 2047-2060 | |
| 45 | Deivi Garcia* | 8 | 2020-2035 | |
| 45 | Dallas Keuchel | 8 | 2012-2027 | |
| 45 | Jarrett Lazarony# | 8 | 2086-2098 | |
| 45 | Antonio Pagan | 8 | 2047-2059 | |
| 45 | Ricardo Raya | 8 | 2030-2045 | |
| 45 | Steve Scruggs | 8 | 2080-2094 | |
| 45 | Mark Wallace | 8 | 2043-2056 | |
| 56 | Jon Arce | 7 | 2031-2045 | |
| 56 | Garçia Bacharel | 7 | 2070-2079 | |
| 56 | Brady Brownfield | 7 | 2025-2041 | |
| 56 | J.B. Bukauskas* | 7 | 2019-2036 | |
| 56 | Juan Castorena | 7 | 2053-2070 | |
| 56 | Pat Champlin | 7 | 2079-2095 | |
| 56 | Liu-chun Cui* | 7 | 2038-2053 | |
| 56 | Greg Earle# | 7 | 2092-2098 | |
| 56 | Leon Estevez# | 7 | 2084-2098 | |
| 56 | Jeurys Familia | 7 | 2012-2032 | |
| 56 | Jeremy Fields | 7 | 2052-2070 | |
| 56 | Danny Fonseca | 7 | 2028-2041 | |
| 56 | Luis Frizzini | 7 | 2071-2085 | |
| 56 | Phil Giorgio | 7 | 2059-2073 | |
| 56 | Izzy Gonzalez | 7 | 2026-2040 | |
| 56 | Dan Howery | 7 | 2034-2051 | |
| 56 | Steven Matz | 7 | 2015-2027 | |
| 56 | Marco McAlonan | 7 | 2042-2056 | |
| 56 | Kyle Milner | 7 | 2084-2096 | |
| 56 | Leo Monrreal* | 7 | 2031-2044 | |
| 56 | Julio Montano | 7 | 2056-2068 | |
| 56 | Andy Pfrommer | 7 | 2020-2041 | |
| 56 | Luis Reinoso | 7 | 2023-2037 | |
| 56 | Jorge Salinas | 7 | 2031-2041 | |
| 56 | Noah Syndergaard | 7 | 2015-2028 | |
| 56 | Nolan Watson | 7 | 2018-2031 | |
| 56 | Jaylen Watts* | 7 | 2067-2086 | |
| 83 | Bob Antoine | 6 | 2040-2047 | |
| 83 | Joe Branham | 6 | 2058-2063 | |
| 83 | Jaime Bunnell | 6 | 2080-2091 | |
| 83 | Jason Chesak | 6 | 2071-2085 | |
| 83 | Mark Crouse | 6 | 2050-2062 | |
| 83 | Jose Cruz# | 6 | 2085-2098 | |
| 83 | Hagen Danner | 6 | 2020-2035 | |
| 83 | Eddie de Dios | 6 | 2029-2044 | |
| 83 | John Decker | 6 | 2062-2076 | |
| 83 | Blake Dickerson# | 6 | 2082-2098 | |
| 83 | Gabe Fay* | 6 | 2069-2089 | |
| 83 | Bobby Fenelon | 6 | 2085-2097 | |
| 83 | Juan Fernandez* | 6 | 2053-2066 | |
| 83 | Robby Gallegos | 6 | 2024-2040 | |
| 83 | James Gilbert | 6 | 2047-2062 | |
| 83 | Tyler Glasnow | 6 | 2017-2030 | |
| 83 | Adam Hammond | 6 | 2023-2028 | |
| 83 | Sam Headlam | 6 | 2042-2055 |
