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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Carlos Crus | 70 | 2006-2013 | |
| 2 | Berend Melman# | 56 | 2026-2030 | |
| 3 | Chris Wallace | 55 | 2016-2020 | |
| 4 | Dave Harrell | 54 | 2002-2008 | |
| 5 | Ted Spencer | 49 | 2008-2011 | |
| 6 | César Delgado | 47 | 2000-2004 | |
| 7 | Ronnie Glass | 46 | 2007-2019 | |
| 8 | Stanley Glavine | 44 | 2006-2011 | |
| 8 | John Owens | 44 | 2008-2015 | |
| 10 | Bob Anderson | 43 | 2017-2020 | |
| 11 | Emílio Aguilar | 42 | 2010-2012 | |
| 11 | Roosevelt Sweeting# | 42 | 2024-2028 | |
| 13 | Jorge Montés# | 41 | 2024-2027 | |
| 14 | Scott Battle | 40 | 2012-2015 | |
| 15 | Melvin Dunn | 38 | 2011-2013 | |
| 16 | Iván Alcocer | 37 | 2005-2016 | |
| 16 | Christopher Burrell | 37 | 2006-2009 | |
| 16 | Tim Pulliam# | 37 | 2022-2024 | |
| 19 | Mike Harper | 36 | 2009-2013 | |
| 19 | Kyle McClellan | 36 | 2008-2013 | |
| 21 | Madison Bumgarner | 35 | 2010-2012 | |
| 21 | Noel Courtney# | 35 | 2024-2027 | |
| 23 | Juan Ayala# | 34 | 2026-2031 | |
| 23 | José Silva# | 34 | 2021-2024 | |
| 23 | Rodney Swain | 34 | 2014-2017 | |
| 26 | Dusty Bowen# | 33 | 2027-2031 | |
| 26 | Casimiro Hall# | 33 | 2025-2028 | |
| 26 | Jack McGinnis# | 33 | 2024-2026 | |
| 26 | Perry van Meggelen# | 33 | 2023-2025 | |
| 30 | Mark Braun# | 32 | 2021-2023 | |
| 30 | Dave Eshelman | 32 | 2009-2012 | |
| 30 | Carlos Rodríguez | 32 | 2008-2014 | |
| 33 | Culley Dodson# | 31 | 2025-2027 | |
| 33 | Domingo Guerrero# | 31 | 2028-2031 | |
| 33 | Abraham Hoover | 31 | 2010-2013 | |
| 33 | Phil Hughes | 31 | 2008-2010 | |
| 33 | Wandy Rodriguez | 31 | 2006-2010 | |
| 33 | Nelson Sandoval | 31 | 2013-2014 | |
| 33 | Jorge Sánchez# | 31 | 2025-2028 | |
| 33 | Robert Weaver | 31 | 2011-2014 | |
| 41 | Archie Anderson | 30 | 2002-2009 | |
| 41 | Bob Anderson | 30 | 2007-2008 | |
| 41 | Ron Blake# | 30 | 2026-2028 | |
| 41 | Glenn Brown | 30 | 2005-2008 | |
| 41 | Malcolm Browning# | 30 | 2025-2030 | |
| 41 | Raúl De Los Santos# | 30 | 2029-2031 | |
| 41 | Leo Erickson# | 30 | 2019-2021 | |
| 41 | Arlen Johnson | 30 | 2007-2014 | |
| 41 | Barney Johnstone# | 30 | 2025-2028 | |
| 41 | Josh MacBrieve | 30 | 2008-2011 | |
| 41 | Vincente Maldonado# | 30 | 2026-2027 | |
| 41 | Todd McElroy | 30 | 2009-2012 | |
| 41 | Tomás Mogarta | 30 | 2016-2020 | |
| 41 | Bartolo Rochel# | 30 | 2028-2031 | |
| 41 | Bennie Rogers# | 30 | 2026-2031 | |
| 56 | James Bates | 29 | 2008-2011 | |
| 56 | Steve Cishek | 29 | 2010-2012 | |
| 56 | Bob Dudley# | 29 | 2025-2027 | |
| 56 | Mike Jeoffrey# | 29 | 2028-2030 | |
| 56 | Phil Lawler | 29 | 2003-2006 | |
| 56 | Bill Lester# | 29 | 2029-2031 | |
| 56 | Greg Little | 29 | 2018-2019 | |
| 56 | Samuel Parrish# | 29 | 2029-2031 | |
| 56 | Mark Rose | 29 | 2005-2008 | |
| 56 | Takashi Saito | 29 | 2007-2021 | |
| 66 | Don Chartrand# | 28 | 2030-2031 | |
| 66 | Wynn Cooke | 28 | 2005-2007 | |
| 66 | Dan Fisher | 28 | 2008-2011 | |
| 66 | José Gutiérrez# | 28 | 2027-2030 | |
| 66 | David Hernández | 28 | 2011-2014 | |
| 66 | Mike Jordan | 28 | 2002-2005 | |
| 66 | Man-ho Kang# | 28 | 2025-2028 | |
| 66 | Cheong-hun Kwon# | 28 | 2024-2027 | |
| 66 | Lance Lynn | 28 | 2010-2013 | |
| 66 | Stu Moore# | 28 | 2025-2027 | |
| 66 | Juan Carlos Peña# | 28 | 2029-2031 | |
| 66 | Roger Powell | 28 | 2017-2019 | |
| 66 | José Pérez | 28 | 2006-2008 | |
| 66 | Carlos Rodríguez# | 28 | 2026-2031 | |
| 66 | Adrián Salazar | 28 | 2005-2014 | |
| 66 | Dave Wheeler | 28 | 2015-2018 | |
| 82 | Jeff Burns | 27 | 2014-2018 | |
| 82 | Joba Chamberlain | 27 | 2008-2009 | |
| 82 | Nick Davis | 27 | 2005-2007 | |
| 82 | Roberto Díaz# | 27 | 2019-2020 | |
| 82 | Orlando Fajardo# | 27 | 2029-2030 | |
| 82 | Zak Fisher# | 27 | 2024-2028 | |
| 82 | Chris Fussell | 27 | 1998-2004 | |
| 82 | Tatsukichi Heida# | 27 | 2029-2031 | |
| 82 | Elvis Lambert | 27 | 2010-2012 | |
| 82 | Kazunari Nishizaki# | 27 | 2026-2029 | |
| 82 | Joaquín Ochoa# | 27 | 2029-2031 | |
| 82 | Víctor Pérez# | 27 | 2028-2031 | |
| 82 | Deron Spears | 27 | 2020-2022 | |
| 82 | Russell Wolff# | 27 | 2029-2030 | |
| 96 | Mike Allen# | 26 | 2027-2029 | |
| 96 | Leone Carnini# | 26 | 2024-2025 | |
| 96 | Héctor Cavallaro# | 26 | 2024-2026 | |
| 96 | Ken Cloude | 26 | 1997-2007 | |
| 96 | Michael Conley | 26 | 2009-2012 |
