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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Doug Hayes | 21 | 1998-2001 | |
| 2 | Li Beggs | 20 | 2012-2015 | |
| 2 | Shawn Locke | 20 | 2012-2015 | |
| 2 | Brian Middleton | 20 | 2000-2003 | |
| 2 | Mike Swanson* | 20 | 2007-2009 | |
| 6 | Greg Forrest | 19 | 2007-2010 | |
| 6 | Allan Howse | 19 | 1998-2001 | |
| 6 | Jimmy McCabe | 19 | 2001-2004 | |
| 9 | Morgan Ackerman | 18 | 1999-2002 | |
| 9 | Peter Bryant | 18 | 2006-2009 | |
| 9 | Norio Hayashi | 18 | 2033-2037 | |
| 9 | Lawrence Columbus LaLoosh* | 18 | 2019-2021 | |
| 9 | Kieran Mabry | 18 | 2032-2036 | |
| 9 | Cisco Ocasio | 18 | 1998-2002 | |
| 15 | Esteban Benítez | 17 | 2001-2003 | |
| 15 | Shane Carr | 17 | 2000-2003 | |
| 15 | Dennis Estep | 17 | 2001-2004 | |
| 15 | Patrick Harding | 17 | 2000-2003 | |
| 15 | Kevin Lee | 17 | 2012-2015 | |
| 15 | Alex Wood | 17 | 2034-2038 | |
| 21 | Dillon Bell | 16 | 2007-2010 | |
| 21 | Gabriel Campos* | 16 | 2005-2008 | |
| 21 | León Costello | 16 | 2005-2008 | |
| 21 | Doug Davis | 16 | 2003-2006 | |
| 21 | Will Franklin | 16 | 2019-2021 | |
| 21 | Kuniaki Ine | 16 | 1999-2002 | |
| 21 | Dwight Johnston | 16 | 2032-2036 | |
| 21 | Daniel King | 16 | 1998-2001 | |
| 21 | David Lewis | 16 | 1998-2002 | |
| 21 | Millard McCoy | 16 | 2017-2019 | |
| 21 | Kelly Morales | 16 | 2033-2037 | |
| 21 | Ricardo Olvera | 16 | 2001-2004 | |
| 21 | Juan Jose Osorio# | 16 | 2059-2062 | |
| 21 | Esteban Rivera | 16 | 2010-2013 | |
| 21 | Jorge Stanza | 16 | 2011-2014 | |
| 21 | Brady Terry | 16 | 1998-2001 | |
| 21 | Dennis Tolbert | 16 | 2000-2002 | |
| 21 | Sinclair Trouwborst | 16 | 2032-2036 | |
| 39 | Félix Abales# | 15 | 2059-2062 | |
| 39 | Oliver Abbott | 15 | 2043-2046 | |
| 39 | Elwood Blues | 15 | 2021-2023 | |
| 39 | Mark Burns | 15 | 2007-2010 | |
| 39 | Preston Callahan | 15 | 2044-2047 | |
| 39 | Will Cameron | 15 | 1998-2000 | |
| 39 | Marcus Coleman | 15 | 2012-2015 | |
| 39 | Domingo Cruz# | 15 | 2059-2062 | |
| 39 | Jim Córdova | 15 | 2033-2037 | |
| 39 | Ramón Farías | 15 | 2009-2012 | |
| 39 | Andrés Ferreira | 15 | 2012-2015 | |
| 39 | Nick Garner | 15 | 2034-2038 | |
| 39 | Duane Grimes | 15 | 2012-2015 | |
| 39 | Xu-gang Li | 15 | 1998-2001 | |
| 39 | Ash Malone | 15 | 2023-2025 | |
| 39 | Troy Preston | 15 | 2018-2021 | |
| 39 | Fernando Rangel | 15 | 2036-2038 | |
| 39 | Marcos Rivas | 15 | 2043-2045 | |
| 39 | Alfredo Salazar | 15 | 2012-2015 | |
| 39 | Skip Stewart | 15 | 2011-2014 | |
| 39 | Joe Taylor | 15 | 2042-2045 | |
| 39 | Steve Thurman | 15 | 2005-2008 | |
| 39 | Dick Trickle III | 15 | 2010-2013 | |
| 39 | Bryan Walden* | 15 | 2005-2008 | |
| 63 | Cade Alexander | 14 | 2034-2038 | |
| 63 | Lawrence Brown | 14 | 2017-2019 | |
| 63 | Roberto Cortéz | 14 | 2007-2009 | |
| 63 | Eric Craigston | 14 | 1998-2001 | |
| 63 | Tully Crow | 14 | 2015-2017 | |
| 63 | Clark Curry# | 14 | 2060-2062 | |
| 63 | Howard Gowing | 14 | 2026-2028 | |
| 63 | Guillermo Gómez | 14 | 2001-2004 | |
| 63 | Jason Hull | 14 | 1998-2000 | |
| 63 | Jamie King | 14 | 1998-2001 | |
| 63 | Jay Lee, Jr. | 14 | 2010-2012 | |
| 63 | Jorge Pereira | 14 | 2010-2012 | |
| 63 | Jarred Perkins | 14 | 2033-2037 | |
| 63 | Jefferson Pierce | 14 | 2031-2033 | |
| 63 | Carlos Rivera | 14 | 2012-2015 | |
| 63 | Lloyd Scott | 14 | 1999-2002 | |
| 63 | Juan Suárez | 14 | 2014-2016 | |
| 63 | Len Tatum | 14 | 2003-2005 | |
| 63 | Junior Valentín | 14 | 2006-2009 | |
| 63 | Manny Vargas | 14 | 2011-2014 | |
| 63 | Grant Wright | 14 | 2032-2036 | |
| 84 | Otis Boudreaux# | 13 | 2054-2056 | |
| 84 | Phil Bridges | 13 | 1998-2001 | |
| 84 | Pavel Bure, Jr. | 13 | 2021-2023 | |
| 84 | Benoît Bélanger | 13 | 2034-2037 | |
| 84 | Fernando Calderón | 13 | 2049-2051 | |
| 84 | Franco Charles | 13 | 2033-2037 | |
| 84 | Alfredo Chávez | 13 | 1999-2002 | |
| 84 | Jeff Clay | 13 | 2002-2004 | |
| 84 | Mike Clifton | 13 | 2006-2009 | |
| 84 | António Correa | 13 | 2015-2017 | |
| 84 | Ramón Delgado | 13 | 2051-2053 | |
| 84 | Júlio Drake# | 13 | 2059-2062 | |
| 84 | Jared Fawsyde | 13 | 2032-2036 | |
| 84 | Jeremy Gaze | 13 | 2003-2005 | |
| 84 | Keith Gillett# | 13 | 2058-2061 | |
| 84 | Skip Glendenning* | 13 | 2009-2012 | |
| 84 | Larry Good | 13 | 2031-2033 |
