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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Mike Rottler# | 47 | 2091-2098 | |
| 2 | Kevin Shaw | 40 | 2071-2074 | |
| 3 | David Ortiz | 39 | 2048-2052 | |
| 4 | Ryan Porterfield# | 38 | 2088-2090 | |
| 5 | Keith Santa Ana# | 37 | 2093-2098 | |
| 6 | Alex Maldonado# | 32 | 2089-2092 | |
| 6 | Jeff Pelt | 32 | 2054-2059 | |
| 8 | Juan Mesa | 31 | 2076-2079 | |
| 9 | Henry Lopez# | 30 | 2091-2096 | |
| 9 | Donovan Presley# | 30 | 2095-2097 | |
| 11 | Nate Washington | 29 | 2044-2046 | |
| 12 | Armando Alvarado | 28 | 2027-2029 | |
| 13 | Aaron Robbins | 27 | 2057-2060 | |
| 14 | Bernie Gomez# | 26 | 2096-2098 | |
| 14 | Kellen Holte | 26 | 2058-2061 | |
| 14 | Nicanor Moledo | 26 | 2051-2053 | |
| 14 | Garrett Patterson | 26 | 2039-2041 | |
| 14 | Raul Valdez# | 26 | 2090-2095 | |
| 19 | Shane Beard | 25 | 2068-2075 | |
| 19 | Adam Kemmerer# | 25 | 2088-2098 | |
| 19 | Andy Savery | 25 | 2049-2051 | |
| 22 | Randy Haynes | 24 | 2087-2095 | |
| 22 | John Penney | 24 | 2047-2049 | |
| 22 | Josh Sheeley# | 24 | 2089-2098 | |
| 22 | Joe Whaley# | 24 | 2095-2098 | |
| 26 | Jose Bautista | 23 | 2028-2032 | |
| 26 | Cesar Contreras# | 23 | 2091-2096 | |
| 26 | Matt Freeman | 23 | 2054-2056 | |
| 26 | Ed Mercado# | 23 | 2090-2094 | |
| 26 | Jose Padilla | 23 | 2049-2050 | |
| 26 | Jeff Zink | 23 | 2055-2058 | |
| 32 | Freddie Colegrove | 22 | 2069-2070 | |
| 32 | Antonio Jimenez# | 22 | 2083-2089 | |
| 32 | Jonathan Martinez | 22 | 2015-2018 | |
| 32 | Jon Sandoval* | 22 | 2049-2051 | |
| 32 | Jake Stevens | 22 | 2005-2009 | |
| 32 | Dale Tatem# | 22 | 2096-2098 | |
| 38 | Esteban Aguirre# | 21 | 2090-2092 | |
| 38 | Tyler Alexander | 21 | 2016-2020 | |
| 38 | Troy Brannon | 21 | 2043-2044 | |
| 38 | Tim Gillon | 21 | 2049-2051 | |
| 38 | Jonathan Gross | 21 | 2071-2072 | |
| 38 | Min-yul Kym# | 21 | 2090-2092 | |
| 38 | Paul Mueller | 21 | 2022-2024 | |
| 38 | Jose Olguin | 21 | 2064-2066 | |
| 38 | Alex Saucedo# | 21 | 2092-2095 | |
| 38 | Justin Steele | 21 | 2017-2020 | |
| 48 | Brendan Burmaster | 20 | 2053-2055 | |
| 48 | Mike Burr | 20 | 2035-2040 | |
| 48 | Jesus Macias | 20 | 2024-2026 | |
| 48 | Bobby Robinson | 20 | 2051-2052 | |
| 52 | Doug Andrews | 19 | 2045-2047 | |
| 52 | Chris Arana | 19 | 2031-2037 | |
| 52 | Jon Bradley | 19 | 2062-2063 | |
| 52 | Brent Brzezinski# | 19 | 2094-2094 | |
| 52 | Joe Campbell# | 19 | 2090-2096 | |
| 52 | Justin Cloonan | 19 | 2063-2064 | |
| 52 | Nelson Cuellar | 19 | 2060-2061 | |
| 52 | Danny Donn | 19 | 2090-2095 | |
| 52 | Terrell Hagans | 19 | 2092-2093 | |
| 52 | Howard Nealon | 19 | 2070-2071 | |
| 52 | Jimmy O'Connor | 19 | 2033-2036 | |
| 52 | Cody Sullens | 19 | 2040-2042 | |
| 64 | Al Arguello | 18 | 2049-2050 | |
| 64 | Andy Beckett | 18 | 2060-2065 | |
| 64 | Alfredo Bengochea | 18 | 2053-2053 | |
| 64 | Jeremy Boehning | 18 | 2046-2047 | |
| 64 | Miguel Cazares# | 18 | 2089-2091 | |
| 64 | Andy Crill | 18 | 2047-2048 | |
| 64 | Enrique Escalante# | 18 | 2091-2095 | |
| 64 | Raul Gonzales | 18 | 2080-2080 | |
| 64 | Jake Jackson | 18 | 2069-2070 | |
| 64 | David Jones | 18 | 2046-2046 | |
| 64 | Angelo Marquez# | 18 | 2096-2098 | |
| 64 | Antonio Ovalles# | 18 | 2094-2096 | |
| 64 | Daniel Payne | 18 | 2023-2024 | |
| 64 | Andrew Peebles | 18 | 2073-2075 | |
| 64 | Tanner Rainey | 18 | 2017-2018 | |
| 64 | Miguel Rubio | 18 | 2048-2049 | |
| 64 | Luis Ruiz# | 18 | 2096-2098 | |
| 81 | Damion Baynard | 17 | 2051-2053 | |
| 81 | Scott Blewett | 17 | 2017-2018 | |
| 81 | Anthony Carter | 17 | 2008-2009 | |
| 81 | Matt Colgan | 17 | 2040-2041 | |
| 81 | Mike Connelly | 17 | 2062-2062 | |
| 81 | Drew Gonzales | 17 | 2047-2056 | |
| 81 | Vinny Gutierrez | 17 | 2082-2083 | |
| 81 | Chad Kenyon | 17 | 2043-2043 | |
| 81 | Chuck Lofgren | 17 | 2006-2006 | |
| 81 | J.D. Martin | 17 | 2003-2006 | |
| 81 | Shane Mazzara | 17 | 2056-2059 | |
| 81 | Eric McClure | 17 | 2053-2054 | |
| 81 | Taylor Misiak | 17 | 2075-2075 | |
| 81 | Vince Schmidt# | 17 | 2092-2095 | |
| 81 | Brady Scott | 17 | 2020-2021 | |
| 81 | Steve Vaillancourt# | 17 | 2095-2096 | |
| 97 | Gus Aguilar# | 16 | 2090-2093 | |
| 97 | Ivan Alfaro | 16 | 2063-2064 | |
| 97 | Ron Allen | 16 | 2060-2062 | |
| 97 | Jung-Keun Bong | 16 | 2000-2001 |
