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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Mike Sweigart# | 31 | 2095-2098 | |
| 2 | Rob Blanton# | 29 | 2091-2095 | |
| 3 | Cody Carroll | 27 | 2016-2021 | |
| 4 | Jeremy Duffy# | 26 | 2089-2092 | |
| 5 | Colin Fleck | 25 | 2060-2063 | |
| 5 | Mario Soto | 25 | 2081-2084 | |
| 7 | Jeff Goodman | 24 | 2053-2059 | |
| 8 | David Sosebee | 21 | 2016-2021 | |
| 8 | Oscar Tamez | 21 | 2045-2049 | |
| 10 | Jerry Jones | 20 | 2069-2071 | |
| 10 | Adrian Mireles | 20 | 2051-2054 | |
| 12 | Alejandro Alvarado# | 19 | 2095-2098 | |
| 12 | Ben Carbaugh | 19 | 2076-2078 | |
| 12 | Mike Collins | 19 | 2073-2075 | |
| 12 | Phil Gibbs# | 19 | 2095-2098 | |
| 12 | Tyler Gilbert | 19 | 2015-2018 | |
| 12 | Steve Levy | 19 | 2067-2069 | |
| 12 | Mark Seyler | 19 | 2015-2021 | |
| 19 | Jeremy Bennett# | 18 | 2097-2098 | |
| 19 | Gary Downey | 18 | 2070-2072 | |
| 19 | Joseph Fisher# | 18 | 2097-2098 | |
| 19 | Ivan Perez# | 18 | 2093-2095 | |
| 19 | Elliott Powell | 18 | 2071-2073 | |
| 24 | Dan Fagan# | 17 | 2095-2097 | |
| 24 | Jesus Morin | 17 | 2050-2051 | |
| 24 | Frank Salazar | 17 | 2066-2069 | |
| 24 | Jason Terry | 17 | 2022-2025 | |
| 24 | Antonio Vidal | 17 | 2051-2053 | |
| 29 | Wiley Hill# | 16 | 2088-2093 | |
| 29 | Adam Kline | 16 | 2077-2079 | |
| 29 | Richard Leshane | 16 | 2028-2029 | |
| 29 | Winston Loredo# | 16 | 2091-2096 | |
| 29 | Justin Mackey# | 16 | 2097-2098 | |
| 29 | Kevin Main# | 16 | 2097-2098 | |
| 29 | Andy Mosebach | 16 | 2072-2073 | |
| 29 | Michael Ouellette | 16 | 2086-2090 | |
| 29 | Angel Perez# | 16 | 2095-2098 | |
| 38 | Brady Aiken | 15 | 2016-2018 | |
| 38 | Jake Desselie# | 15 | 2088-2090 | |
| 38 | Felipe Dirzo | 15 | 2032-2033 | |
| 38 | Jeff Downing# | 15 | 2088-2090 | |
| 38 | Mike Fluitt | 15 | 2081-2084 | |
| 38 | Jay Foley | 15 | 2059-2061 | |
| 38 | Pete Friedman# | 15 | 2096-2097 | |
| 38 | Marvin Gonzales | 15 | 2049-2054 | |
| 38 | Kiambu Hight | 15 | 2076-2078 | |
| 38 | Danny Hoaglund | 15 | 2059-2060 | |
| 38 | Dan Lash# | 15 | 2096-2097 | |
| 38 | Jonas McHugh | 15 | 2061-2062 | |
| 38 | Oscar Palomares | 15 | 2029-2031 | |
| 38 | Josh Roeder | 15 | 2015-2021 | |
| 52 | Carlos Bodden# | 14 | 2092-2095 | |
| 52 | Chris Cisek | 14 | 2064-2064 | |
| 52 | Chris Day | 14 | 2085-2086 | |
| 52 | Rich Dunham | 14 | 2049-2050 | |
| 52 | Travis Edwards | 14 | 2045-2048 | |
| 52 | John Grady | 14 | 2053-2054 | |
| 52 | Jose Mendez | 14 | 2071-2073 | |
| 52 | Francisco Michel | 14 | 2077-2078 | |
| 52 | Hunter Parkinson | 14 | 2018-2020 | |
| 52 | Danny Pasciak | 14 | 2060-2063 | |
| 52 | David Roldan# | 14 | 2094-2095 | |
| 52 | Ismael Santiago | 14 | 2047-2050 | |
| 52 | Franklin Velasquez | 14 | 2073-2075 | |
| 52 | Nick Zahradka# | 14 | 2095-2097 | |
| 66 | Jorge Abreu | 13 | 2022-2024 | |
| 66 | Edwin Aguirre | 13 | 2044-2045 | |
| 66 | Josh Bell | 13 | 2064-2064 | |
| 66 | Mike Brown# | 13 | 2095-2096 | |
| 66 | Luis E. Cedeno | 13 | 2015-2018 | |
| 66 | Matt Clancy | 13 | 2017-2021 | |
| 66 | Ricky Diaz | 13 | 2054-2056 | |
| 66 | Shigem Hirata# | 13 | 2092-2094 | |
| 66 | Kyle Horn# | 13 | 2093-2093 | |
| 66 | Danny Jaramillo# | 13 | 2092-2096 | |
| 66 | Bob Love# | 13 | 2096-2097 | |
| 66 | John McDonald | 13 | 2054-2055 | |
| 66 | Jon Medina | 13 | 2075-2075 | |
| 66 | Mel Medina | 13 | 2030-2031 | |
| 66 | Ben Mills# | 13 | 2097-2098 | |
| 66 | Jeremy Nelson | 13 | 2068-2070 | |
| 66 | Felix Nieto | 13 | 2072-2072 | |
| 66 | Roberto Novoa | 13 | 2001-2002 | |
| 66 | Jason Pressley# | 13 | 2098-2098 | |
| 66 | Rene Ramos | 13 | 2054-2056 | |
| 66 | Julio Rolon# | 13 | 2097-2097 | |
| 66 | Rico Rolon | 13 | 2042-2043 | |
| 66 | Jonathan Santiago | 13 | 2050-2055 | |
| 66 | Justin Scott# | 13 | 2093-2093 | |
| 66 | Steve Shepard | 13 | 2060-2061 | |
| 91 | Ricky Alejandro | 12 | 2083-2084 | |
| 91 | Pat Bachor# | 12 | 2088-2091 | |
| 91 | Paul Blair# | 12 | 2086-2089 | |
| 91 | Oreste Ciottone# | 12 | 2093-2094 | |
| 91 | Ian Dery# | 12 | 2094-2096 | |
| 91 | Josh Erickson | 12 | 2075-2075 | |
| 91 | Ismael Espaillat# | 12 | 2087-2087 | |
| 91 | James Hawkins# | 12 | 2095-2097 | |
| 91 | Mario Marquez | 12 | 2050-2056 | |
| 91 | Ottaviano Messori | 12 | 2059-2059 |
