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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Marcos Juarez | 65 | 2072-2083 | |
| 2 | Eddie Russo | 63 | 2082-2094 | |
| 3 | David Mendoza | 51 | 2075-2092 | |
| 4 | Glen Sweigart | 50 | 2031-2036 | |
| 5 | Jake Corson | 46 | 2027-2031 | |
| 5 | Godfrey Poldervaart | 46 | 2052-2056 | |
| 7 | Steve Jordison# | 45 | 2091-2097 | |
| 8 | Felix Aguilar | 43 | 2026-2035 | |
| 8 | Pablo Garza | 43 | 2056-2062 | |
| 10 | Davin Lindsey# | 41 | 2091-2096 | |
| 11 | George Bartlett | 39 | 2046-2051 | |
| 11 | Josh Beal | 39 | 2084-2093 | |
| 11 | Mark Boggs | 39 | 2084-2094 | |
| 14 | Dan Cleary | 38 | 2067-2069 | |
| 15 | Ryan Dooley | 37 | 2050-2052 | |
| 15 | John Knowlden | 37 | 2083-2094 | |
| 15 | Roberto Ojeda | 37 | 2028-2030 | |
| 18 | Luis Robles | 36 | 2066-2075 | |
| 19 | Tom Ayars | 35 | 2027-2035 | |
| 19 | Mike Baker | 35 | 2074-2076 | |
| 19 | C.J. Doane | 35 | 2074-2076 | |
| 19 | Alec Kovach | 35 | 2083-2085 | |
| 23 | Ryan Dzik | 34 | 2084-2091 | |
| 23 | Justin Hedges | 34 | 2089-2093 | |
| 23 | Ross Jenkins | 34 | 2032-2036 | |
| 23 | Noah Murdock | 34 | 2016-2020 | |
| 23 | Jared Petersen# | 34 | 2093-2096 | |
| 23 | Alejandro Sanchez | 34 | 2080-2087 | |
| 23 | Eric Thorn | 34 | 2054-2055 | |
| 30 | Willie Claros | 33 | 2048-2049 | |
| 30 | Dan Jedlicka | 33 | 2081-2089 | |
| 30 | Mike Kosloski# | 33 | 2088-2091 | |
| 30 | Drew Mackie | 33 | 2072-2073 | |
| 30 | Jeff Schildt# | 33 | 2090-2098 | |
| 30 | Craig Windt | 33 | 2081-2092 | |
| 36 | Eric Field | 32 | 2046-2049 | |
| 36 | Josh Millender | 32 | 2080-2084 | |
| 36 | Doug Whitmore | 32 | 2030-2034 | |
| 39 | Charlie Grafman | 31 | 2076-2085 | |
| 39 | Charlie Hayden | 31 | 2049-2057 | |
| 39 | Daniel Jenney# | 31 | 2095-2098 | |
| 39 | Eric Lehman# | 31 | 2090-2095 | |
| 39 | Paul Naranjo | 31 | 2027-2037 | |
| 39 | Dennis Oliveri# | 31 | 2093-2095 | |
| 45 | Jesus Campos# | 30 | 2094-2096 | |
| 45 | Jose Chavez | 30 | 2050-2051 | |
| 45 | Paul Crowe | 30 | 2078-2089 | |
| 45 | Rey Hernandez | 30 | 2071-2079 | |
| 45 | Ezra Peach | 30 | 2024-2030 | |
| 45 | Alberto Quinonez | 30 | 2050-2057 | |
| 45 | Alex Robson | 30 | 2026-2028 | |
| 45 | Grant Watson | 30 | 2017-2021 | |
| 45 | Joe Wieland | 30 | 2017-2019 | |
| 54 | Chris Bartlett | 29 | 2036-2038 | |
| 54 | Ray Draus# | 29 | 2092-2096 | |
| 54 | Elijah Dyson | 29 | 2052-2053 | |
| 54 | Javier Flores | 29 | 2040-2051 | |
| 54 | Jose Hinojosa# | 29 | 2089-2095 | |
| 54 | Mike Holt | 29 | 2044-2050 | |
| 54 | Rafael Juarez | 29 | 2027-2039 | |
| 54 | Alex Lozano | 29 | 2092-2094 | |
| 54 | Jairo Olcese# | 29 | 2097-2098 | |
| 54 | Hugo Ramirez | 29 | 2052-2056 | |
| 54 | Dave Ruiz | 29 | 2083-2096 | |
| 54 | Steven Wright | 29 | 2008-2014 | |
| 66 | Oscar Borjas | 28 | 2048-2051 | |
| 66 | Jairo Calleros | 28 | 2024-2025 | |
| 66 | Zach Clark | 28 | 2008-2013 | |
| 66 | Fausto Cossiga | 28 | 2067-2069 | |
| 66 | Ben King | 28 | 2072-2078 | |
| 66 | Austin Kubitza | 28 | 2015-2017 | |
| 66 | Eric Muse | 28 | 2075-2080 | |
| 66 | Yohan Pino | 28 | 2007-2012 | |
| 66 | Steve Powers# | 28 | 2094-2096 | |
| 66 | Alex Ramirez | 28 | 2044-2051 | |
| 66 | Kevin Roberts | 28 | 2073-2075 | |
| 66 | Tim Ryan | 28 | 2026-2028 | |
| 66 | Warwick Saupold | 28 | 2013-2018 | |
| 66 | Steve Tamburrino | 28 | 2084-2090 | |
| 66 | Ivan Vidales# | 28 | 2091-2092 | |
| 66 | Gillian Wernet | 28 | 2022-2027 | |
| 82 | Yadier Alvarez | 27 | 2021-2031 | |
| 82 | Steven Arnold | 27 | 2040-2041 | |
| 82 | Ed Bain | 27 | 2060-2064 | |
| 82 | Jeff Barbour | 27 | 2039-2049 | |
| 82 | Kevin Bray | 27 | 2069-2074 | |
| 82 | Jeff Burgei | 27 | 2073-2079 | |
| 82 | Ryan Caruso | 27 | 2034-2039 | |
| 82 | Ryan Clark | 27 | 2069-2074 | |
| 82 | Ken Coston | 27 | 2047-2054 | |
| 82 | Jose Diaz# | 27 | 2085-2091 | |
| 82 | Jeremy Johnson | 27 | 2028-2032 | |
| 82 | Juan Macias | 27 | 2074-2080 | |
| 82 | Josh McVaney# | 27 | 2092-2095 | |
| 82 | Steve Shepard | 27 | 2062-2064 | |
| 82 | Hector Silva | 27 | 2067-2070 | |
| 82 | Andy Stone | 27 | 2051-2053 | |
| 82 | Corey Story | 27 | 2070-2079 | |
| 82 | Chris Tracey | 27 | 2066-2069 | |
| 82 | Jake Wahlstrom# | 27 | 2094-2098 |
