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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jason Creasy | 90 | 2016-2027 | |
| 2 | Jorge García | 89 | 2054-2067 | |
| 3 | Brenden Backhouse | 85 | 2021-2028 | |
| 4 | Chris Griffith | 84 | 2048-2059 | |
| 5 | Brandon Workman | 80 | 2013-2023 | |
| 6 | Stanley Brown | 77 | 2053-2064 | |
| 7 | Juan Hernández | 72 | 2055-2063 | |
| 8 | Daniel Young | 68 | 2049-2060 | |
| 9 | Bohdan Grady | 67 | 2025-2033 | |
| 10 | Jon Feldbaek# | 64 | 2058-2066 | |
| 10 | Vidal Nuno | 64 | 2013-2022 | |
| 12 | Shawn Davis | 63 | 2021-2027 | |
| 12 | Ron Rey# | 63 | 2058-2067 | |
| 12 | Flynn Wallace | 63 | 2037-2044 | |
| 15 | Stef van der Meulen | 61 | 2027-2039 | |
| 15 | Tyler Waldron | 61 | 2014-2022 | |
| 17 | Mark Helen | 60 | 2054-2062 | |
| 18 | John Cutler | 59 | 2022-2032 | |
| 18 | Matt Maloney | 59 | 2007-2016 | |
| 18 | Werner Pettwa | 59 | 2055-2063 | |
| 18 | Willie Reynolds | 59 | 2034-2041 | |
| 22 | Isaac Aldridge | 58 | 2048-2063 | |
| 22 | Jordan Armstrong | 58 | 2053-2066 | |
| 22 | Erik Blanton | 58 | 2021-2028 | |
| 22 | Corey Kluber | 58 | 2010-2017 | |
| 26 | Jerry Baker# | 57 | 2056-2066 | |
| 26 | Mike Queza | 57 | 2052-2057 | |
| 26 | Larry Stanley | 57 | 2039-2046 | |
| 29 | Stolm Moore | 56 | 2050-2058 | |
| 29 | Chad Page | 56 | 2053-2065 | |
| 29 | Ryan Williamson | 56 | 2037-2051 | |
| 32 | Ken McLeod# | 55 | 2054-2067 | |
| 33 | Eitel Arnold | 54 | 2035-2050 | |
| 33 | Tolentino Reis | 54 | 2046-2059 | |
| 35 | David Anderson# | 53 | 2061-2066 | |
| 35 | Nick Compton | 53 | 2032-2042 | |
| 35 | Gilbert Crowe | 53 | 2049-2059 | |
| 35 | Marvin Valenzuela | 53 | 2034-2041 | |
| 39 | Mark Bartlett# | 52 | 2056-2067 | |
| 39 | Phil Irwin | 52 | 2012-2019 | |
| 39 | Lindsay Johnston | 52 | 2030-2039 | |
| 39 | Levi van der Star | 52 | 2020-2031 | |
| 39 | Bob Wood | 52 | 2039-2052 | |
| 44 | Ben Herring | 51 | 2051-2063 | |
| 44 | Sébastien Maire | 51 | 2052-2067 | |
| 46 | Hugh Beck | 50 | 2055-2064 | |
| 46 | D.J. Brown | 50 | 2014-2025 | |
| 46 | Carlos Carrasco | 50 | 2008-2015 | |
| 46 | Patrick Cooper | 50 | 2014-2018 | |
| 46 | Jejomar Guzman | 50 | 2046-2059 | |
| 46 | Will McKeaver | 50 | 2027-2038 | |
| 46 | Doug Parsons | 50 | 2047-2059 | |
| 46 | Ludovic Pinel | 50 | 2052-2059 | |
| 54 | Kevin Brady | 49 | 2016-2026 | |
| 54 | Michael Colla | 49 | 2013-2018 | |
| 54 | Milan Fanfulik# | 49 | 2059-2066 | |
| 57 | Bob Fowler | 48 | 2051-2060 | |
| 57 | Mitch Richardson | 48 | 2032-2041 | |
| 57 | Fernando Sáenz# | 48 | 2052-2067 | |
| 57 | Mike Tate | 48 | 2050-2057 | |
| 61 | Noé Bessé | 47 | 2031-2039 | |
| 61 | Tusya Eremei# | 47 | 2052-2067 | |
| 61 | Keiji Fujihara | 47 | 2036-2042 | |
| 61 | Raúl Garza | 47 | 2037-2046 | |
| 61 | Trofimoff Mezenov# | 47 | 2058-2067 | |
| 61 | Chad Rogers | 47 | 2014-2018 | |
| 61 | Fikri Rûmî# | 47 | 2059-2065 | |
| 61 | Dan Slania | 47 | 2017-2032 | |
| 61 | Víctor Soto | 47 | 2052-2063 | |
| 61 | Sven van der Dusse | 47 | 2050-2063 | |
| 71 | Adam Abbasi# | 46 | 2050-2065 | |
| 71 | Brandon Brown# | 46 | 2053-2060 | |
| 71 | Travis Curry | 46 | 2046-2053 | |
| 71 | Carlos Durán | 46 | 2033-2044 | |
| 71 | Celalettin Ebûssüûd | 46 | 2040-2045 | |
| 71 | Lucas Harrell | 46 | 2009-2021 | |
| 71 | Ryan Herschel | 46 | 2039-2046 | |
| 71 | Fritz Jakkelsen | 46 | 2053-2065 | |
| 71 | Valter Telling# | 46 | 2053-2067 | |
| 80 | Paul Blaine | 45 | 2045-2058 | |
| 80 | Orvo Boberg# | 45 | 2061-2067 | |
| 80 | Joe Cannon | 45 | 2027-2033 | |
| 80 | Harry Cooke | 45 | 2038-2045 | |
| 80 | Martin Guzmán# | 45 | 2057-2067 | |
| 80 | David Hale | 45 | 2013-2020 | |
| 80 | Devin Jones | 45 | 2014-2019 | |
| 80 | Dan Mahoney | 45 | 2014-2022 | |
| 80 | José Martínez | 45 | 2047-2055 | |
| 80 | John Merritt | 45 | 2030-2034 | |
| 80 | Bernardo Morales | 45 | 2053-2066 | |
| 80 | Juan Peña# | 45 | 2056-2067 | |
| 80 | Jamal Raynaud | 45 | 2026-2038 | |
| 80 | Carlos Rocha | 45 | 2054-2064 | |
| 80 | Joe Rodríguez# | 45 | 2064-2067 | |
| 80 | Héctor Rojas | 45 | 2058-2063 | |
| 80 | Anthony Thomas | 45 | 2049-2055 | |
| 80 | Dave Whitfield# | 45 | 2057-2063 | |
| 98 | Dario Agrazal | 44 | 2019-2031 | |
| 98 | Thiago Bartol | 44 | 2031-2038 | |
| 98 | David Huff | 44 | 2008-2013 |
