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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Matt Maudsley# | 63 | 2091-2098 | |
| 2 | Matt Rutkowski | 51 | 2066-2069 | |
| 3 | Ian Langer# | 41 | 2094-2097 | |
| 4 | Israel Pena# | 40 | 2088-2095 | |
| 4 | Steve Thornton# | 40 | 2094-2096 | |
| 6 | Juan Chavez# | 39 | 2089-2092 | |
| 6 | Jay Wells# | 39 | 2093-2096 | |
| 8 | Francis Martes | 38 | 2017-2022 | |
| 8 | Steve Pritchard# | 38 | 2091-2096 | |
| 8 | Billy Rollins# | 38 | 2095-2098 | |
| 8 | Aaron Whanger | 38 | 2061-2068 | |
| 12 | Javier Encarnacion# | 37 | 2091-2095 | |
| 12 | Adam Lyons# | 37 | 2092-2095 | |
| 12 | Pramana Pamungkas | 37 | 2047-2052 | |
| 12 | Nelson Villa | 37 | 2070-2073 | |
| 16 | Pat Baird# | 36 | 2094-2098 | |
| 17 | Antonio Castillo | 35 | 2046-2050 | |
| 17 | Mark Musacchia | 35 | 2064-2069 | |
| 17 | Paul Wells | 35 | 2050-2052 | |
| 20 | Johnny Alvarado# | 34 | 2093-2096 | |
| 20 | Carlos Saldana | 34 | 2029-2030 | |
| 22 | Archie Bradley | 33 | 2013-2017 | |
| 22 | Ricky Segura | 33 | 2076-2078 | |
| 22 | Harry Turpin | 33 | 2064-2069 | |
| 25 | Paul English | 32 | 2080-2087 | |
| 25 | Giacobbe Luttazi | 32 | 2074-2077 | |
| 25 | Jim Magrane | 32 | 2001-2006 | |
| 28 | Justin Nygard# | 31 | 2091-2095 | |
| 28 | Jeff Schrenk | 31 | 2069-2070 | |
| 30 | Ryan Bowyer | 30 | 2066-2067 | |
| 30 | Justin Duenwald | 30 | 2080-2084 | |
| 30 | Steve Easters | 30 | 2083-2091 | |
| 30 | Casey Maynard# | 30 | 2090-2098 | |
| 30 | Nick Norville# | 30 | 2092-2096 | |
| 30 | Clayton Wilson | 30 | 2047-2049 | |
| 36 | Prospero Bastardo | 29 | 2071-2073 | |
| 36 | Connor Darling | 29 | 2019-2024 | |
| 36 | Steve Ferguson# | 29 | 2090-2094 | |
| 36 | Steve Gaskamp | 29 | 2029-2032 | |
| 36 | Adrian Giraldo# | 29 | 2093-2094 | |
| 36 | Bill Hamilton | 29 | 2057-2058 | |
| 36 | Victor Ontiveros# | 29 | 2095-2097 | |
| 36 | Byron Robinson | 29 | 2038-2041 | |
| 36 | Jared Savage# | 29 | 2085-2092 | |
| 36 | Alex Speas | 29 | 2021-2027 | |
| 46 | Billy Armstrong | 28 | 2045-2051 | |
| 46 | Matt Ball | 28 | 2019-2027 | |
| 46 | Mark Brendemuehl | 28 | 2057-2063 | |
| 46 | Rick DeGeorge | 28 | 2043-2045 | |
| 46 | Garrett Fulenchek | 28 | 2018-2021 | |
| 46 | Ray Goodrum# | 28 | 2094-2097 | |
| 46 | Raul Guerrero | 28 | 2073-2076 | |
| 46 | Santos Lopez | 28 | 2051-2055 | |
| 46 | John McWilliams# | 28 | 2091-2092 | |
| 46 | Joe Slayton# | 28 | 2090-2095 | |
| 56 | Sean Bodrick# | 27 | 2094-2096 | |
| 56 | Chris Bonds# | 27 | 2093-2098 | |
| 56 | Carlos Cheverez | 27 | 2036-2042 | |
| 56 | Chris Clouse | 27 | 2034-2038 | |
| 56 | Jay Cook | 27 | 2089-2091 | |
| 56 | David Hodges | 27 | 2042-2044 | |
| 56 | Jeff Jones# | 27 | 2087-2097 | |
| 56 | Joe Kriss# | 27 | 2084-2091 | |
| 56 | Julio Leal | 27 | 2076-2078 | |
| 56 | Brian McConnell | 27 | 2076-2078 | |
| 56 | Chris Schanz | 27 | 2080-2091 | |
| 67 | Travis Chick | 26 | 2005-2009 | |
| 67 | Alex Cintron | 26 | 2055-2058 | |
| 67 | Eric Davis# | 26 | 2095-2096 | |
| 67 | Joe Gandee | 26 | 2049-2051 | |
| 67 | Marquis Knott | 26 | 2078-2080 | |
| 67 | Juan Rivera | 26 | 2086-2090 | |
| 67 | Brad Scott | 26 | 2070-2072 | |
| 67 | You-yi Xú | 26 | 2031-2040 | |
| 67 | Alex Young | 26 | 2018-2023 | |
| 76 | Bill Amparan# | 25 | 2095-2096 | |
| 76 | Mike Bergeron | 25 | 2071-2073 | |
| 76 | Lorenzo Flecha# | 25 | 2091-2097 | |
| 76 | Cason Greathouse | 25 | 2021-2022 | |
| 76 | Matt Grimm | 25 | 2038-2040 | |
| 76 | Keith Karr# | 25 | 2091-2094 | |
| 76 | Kevin Lavis | 25 | 2071-2075 | |
| 76 | Eric Lawrence# | 25 | 2095-2098 | |
| 76 | Zachery Linker | 25 | 2083-2084 | |
| 76 | Will Nicholas | 25 | 2078-2084 | |
| 76 | Nic Ungs | 25 | 2003-2008 | |
| 76 | Ryan Wilson | 25 | 2089-2092 | |
| 88 | Chris Adler | 24 | 2031-2032 | |
| 88 | Josh Conlan# | 24 | 2096-2098 | |
| 88 | Alex Faedo | 24 | 2020-2023 | |
| 88 | Zack Godley | 24 | 2015-2019 | |
| 88 | Ismael Guillon | 24 | 2016-2019 | |
| 88 | Rick Johnson | 24 | 2037-2038 | |
| 88 | Sam Johnson# | 24 | 2087-2098 | |
| 88 | Ryan Mann# | 24 | 2091-2096 | |
| 88 | Troy McCrackin | 24 | 2040-2042 | |
| 88 | Daniel McGrath | 24 | 2017-2019 | |
| 88 | Josh McKenna# | 24 | 2083-2087 | |
| 88 | Willie Menchaca | 24 | 2030-2031 | |
| 88 | Jose Moravia | 24 | 2052-2054 |
