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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Juan López | 158 | 2029-2044 | |
| 2 | Orlando Zavala | 90 | 2028-2045 | |
| 3 | Dennis Flynn | 79 | 2014-2028 | |
| 4 | Tom Mays | 78 | 2004-2012 | |
| 4 | Mike Saunders | 78 | 2018-2025 | |
| 6 | Mark Charles | 76 | 1994-2007 | |
| 7 | Will Blair | 75 | 2005-2014 | |
| 7 | Lance Carlson | 75 | 2046-2060 | |
| 9 | Geer Pels | 73 | 2049-2058 | |
| 10 | Orlando Espinosa | 72 | 2025-2038 | |
| 10 | Jorge Gómez | 72 | 1992-2004 | |
| 12 | Joseph Powers | 71 | 2024-2038 | |
| 12 | Jonathon Roesler | 71 | 2030-2036 | |
| 14 | Iván Ortíz | 70 | 2027-2034 | |
| 14 | Taizo Yamashita | 70 | 2017-2030 | |
| 16 | Jeff Miller | 69 | 1998-2006 | |
| 16 | Ánibal Moya | 69 | 2007-2018 | |
| 18 | José Serrano | 67 | 2024-2031 | |
| 19 | Duane Bear | 65 | 2024-2032 | |
| 19 | Andrés Campos | 65 | 2003-2012 | |
| 19 | José Flores | 65 | 2030-2039 | |
| 19 | David Gore | 65 | 2021-2027 | |
| 23 | Ánibal Archuleta | 64 | 1992-2007 | |
| 23 | John Cooper | 64 | 2038-2053 | |
| 25 | Bob Boyce | 63 | 2016-2024 | |
| 25 | Paul Burton | 63 | 1997-2007 | |
| 27 | José Rodríguez | 62 | 2045-2058 | |
| 28 | Bengt Broos | 61 | 2054-2063 | |
| 28 | Brodie Hynes | 61 | 2017-2023 | |
| 28 | Luis Maes | 61 | 2004-2015 | |
| 28 | Lúcio Olvera | 61 | 2018-2030 | |
| 28 | Colton Welch | 61 | 1997-2007 | |
| 33 | Gabriel Carrillo | 60 | 2057-2063 | |
| 33 | Micah Moran | 60 | 2013-2019 | |
| 33 | Eduardo Pérez | 60 | 2012-2017 | |
| 36 | Millard Bolton | 59 | 1991-2002 | |
| 36 | Dennis Hartman | 59 | 2048-2058 | |
| 38 | Ronald Ball | 58 | 2024-2038 | |
| 38 | Lawrence Boulter | 58 | 2024-2034 | |
| 38 | Wibren Gouloze | 58 | 2020-2028 | |
| 38 | Ron Taylor | 58 | 1998-2005 | |
| 42 | Alejandro Fuentes | 57 | 2040-2049 | |
| 42 | Alex Harris | 57 | 2027-2044 | |
| 44 | Dave Martinez | 56 | 2063-2069 | |
| 44 | Craig Meyers | 56 | 2041-2051 | |
| 44 | Christopher Wicks | 56 | 1997-2010 | |
| 47 | John Andrasko | 55 | 2061-2069 | |
| 47 | Víctor Flores | 55 | 2009-2014 | |
| 47 | Lorenzo Iuliano | 55 | 2019-2025 | |
| 47 | Colin Moran | 55 | 2017-2023 | |
| 47 | Andrew Rice | 55 | 1990-1995 | |
| 47 | Kyle Ropley | 55 | 2018-2025 | |
| 53 | Robbie DeBalliol | 54 | 2029-2042 | |
| 53 | Chris Thomas | 54 | 1990-1999 | |
| 55 | George Bryant | 53 | 2030-2042 | |
| 55 | Scott de Weever | 53 | 2048-2062 | |
| 55 | José Reyes | 53 | 1994-2000 | |
| 58 | Otto Bannatyne | 52 | 2033-2045 | |
| 58 | Pedro García | 52 | 2005-2012 | |
| 58 | Mike Hayward | 52 | 2058-2066 | |
| 58 | Hae-nim Huh | 52 | 2055-2062 | |
| 58 | Henry Warner | 52 | 2030-2040 | |
| 63 | John Banks | 51 | 2018-2025 | |
| 63 | Ron Bullard | 51 | 2004-2013 | |
| 63 | Sandro Fardelhoa | 51 | 2023-2027 | |
| 63 | Joe Ferguson | 51 | 2062-2067 | |
| 63 | José Hernández | 51 | 1996-2007 | |
| 63 | Francisco Ibarra | 51 | 2018-2023 | |
| 63 | Nobuhito Kobayashi | 51 | 2052-2063 | |
| 63 | Carlos Ramos | 51 | 2023-2034 | |
| 63 | Jesús Reyna | 51 | 2004-2015 | |
| 63 | Carlos Vázquez | 51 | 2045-2055 | |
| 73 | Juan Jose Alvarado | 50 | 1991-1998 | |
| 73 | Reginald Michael | 50 | 2037-2050 | |
| 73 | John Scott | 50 | 2000-2009 | |
| 73 | Javier Valverde | 50 | 2049-2056 | |
| 77 | Dave Jackson | 49 | 2004-2011 | |
| 77 | Scott Randell# | 49 | 2066-2075 | |
| 77 | Brad Skyrme | 49 | 2048-2055 | |
| 77 | Maikel Solano | 49 | 2060-2065 | |
| 81 | Pat Boudreau | 48 | 2042-2053 | |
| 81 | Burt Kuhn | 48 | 1990-1997 | |
| 81 | Justin Morash | 48 | 2031-2041 | |
| 81 | Orlando Álvarez | 48 | 2029-2035 | |
| 85 | Ronald Coleman | 47 | 1990-1995 | |
| 85 | Robby George | 47 | 2007-2016 | |
| 85 | Mike Rempel# | 47 | 2064-2069 | |
| 88 | Naruhiko Abe | 46 | 2023-2032 | |
| 88 | Stan Criner | 46 | 2008-2011 | |
| 88 | Ken Gunn | 46 | 2003-2011 | |
| 88 | Travis McCarthy | 46 | 2004-2016 | |
| 88 | Jeremy McKinley | 46 | 2012-2017 | |
| 88 | Larry Mears | 46 | 2063-2071 | |
| 88 | Clay Quain | 46 | 2034-2044 | |
| 88 | Hughie Ryan | 46 | 2055-2062 | |
| 88 | Rupert Wichers | 46 | 2058-2067 | |
| 97 | Ray Battaglia | 45 | 2068-2074 | |
| 97 | Walt Hulshof | 45 | 2057-2066 | |
| 97 | Michael Kramer | 45 | 1991-2004 | |
| 97 | Jerry Moss | 45 | 2057-2066 |
