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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jason Kennedy | 60 | 2013-2018 | |
| 2 | Christian Hamilton | 53 | 2016-2020 | |
| 3 | Willie Campbell | 50 | 2016-2021 | |
| 3 | Bob Lewis | 50 | 2018-2022 | |
| 3 | Mike Smith | 50 | 2015-2019 | |
| 6 | Rob Berry | 49 | 2015-2019 | |
| 6 | Tim Lincecum | 49 | 2004-2007 | |
| 6 | Javier Pineda | 49 | 2016-2020 | |
| 9 | Bob Schultz | 48 | 2006-2009 | |
| 9 | Ilinian Thaqi | 48 | 2018-2022 | |
| 11 | Kenny Carlson | 47 | 2016-2019 | |
| 12 | Mal Bascombe | 46 | 2018-2022 | |
| 12 | Daniel Drouin | 46 | 2018-2022 | |
| 12 | Stu Gentry | 46 | 2013-2018 | |
| 12 | Edward Jones | 46 | 2015-2019 | |
| 12 | Bryan O'Morgan | 46 | 2016-2021 | |
| 12 | Alfredo Vázquez | 46 | 2015-2019 | |
| 18 | Garry Gibson | 45 | 2006-2009 | |
| 18 | Josh Ortíz | 45 | 2017-2021 | |
| 20 | Matt Carlisle | 44 | 2014-2018 | |
| 20 | Millard MacGilchrist | 44 | 2016-2021 | |
| 20 | Luca Mannino | 44 | 2012-2017 | |
| 20 | Lee Myers# | 44 | 2016-2017 | |
| 24 | Jon Bennett | 43 | 2016-2018 | |
| 24 | Francisco Castro | 43 | 2016-2020 | |
| 24 | Sergio García | 43 | 2018-2022 | |
| 24 | Kiyomori Hirano# | 43 | 2028-2031 | |
| 24 | Sun Kang# | 43 | 2025-2028 | |
| 24 | Dave Kent | 43 | 2013-2017 | |
| 24 | Lindsay Page | 43 | 2016-2019 | |
| 31 | Josh Brown | 42 | 2007-2009 | |
| 31 | Doug Fister | 42 | 2005-2008 | |
| 31 | Tatsukichi Heida# | 42 | 2024-2027 | |
| 31 | Phil Kelly | 42 | 2016-2020 | |
| 31 | Matt Knight | 42 | 2015-2019 | |
| 31 | James MacPherson | 42 | 2016-2020 | |
| 31 | Dan Moore | 42 | 2016-2021 | |
| 31 | Bill Pearce | 42 | 2014-2018 | |
| 31 | Pedro Ritodíaz | 42 | 2016-2020 | |
| 40 | Juan Guillén# | 41 | 2028-2031 | |
| 40 | Dick Hulse | 41 | 2004-2007 | |
| 40 | John Jackson | 41 | 2016-2020 | |
| 40 | Ateþ Kazancigil | 41 | 2018-2022 | |
| 40 | Mat Latos | 41 | 2006-2009 | |
| 40 | Kris Medlen | 41 | 2006-2009 | |
| 40 | Dale Powell | 41 | 2016-2020 | |
| 40 | Chris Rodríguez | 41 | 2018-2022 | |
| 40 | Javier Trujillo# | 41 | 2024-2027 | |
| 40 | Avery Warren | 41 | 2016-2020 | |
| 50 | Scott Hoover | 40 | 2018-2022 | |
| 50 | Billy Johnson | 40 | 2018-2022 | |
| 50 | Jonah Keller | 40 | 2016-2020 | |
| 50 | Jim MacKey | 40 | 2012-2017 | |
| 50 | Brandon Morrow | 40 | 2004-2007 | |
| 50 | Francisco Olivarez# | 40 | 2024-2027 | |
| 50 | Orlando Rocha | 40 | 2016-2020 | |
| 50 | Joe Taylor | 40 | 2016-2020 | |
| 50 | Ricardo Valdés# | 40 | 2024-2027 | |
| 50 | Ramón Villalobos# | 40 | 2025-2028 | |
| 50 | Kevin Welch | 40 | 2017-2021 | |
| 50 | Allen Williamson | 40 | 2017-2021 | |
| 50 | Joe Wynn | 40 | 2018-2022 | |
| 63 | Calvin Anderson | 39 | 2018-2022 | |
| 63 | Gabriel Antúnez# | 39 | 2025-2028 | |
| 63 | Arlen Davis | 39 | 2013-2018 | |
| 63 | Martín Estrada# | 39 | 2028-2031 | |
| 63 | Ramón Herrera | 39 | 2016-2020 | |
| 63 | Michel Keller# | 39 | 2025-2028 | |
| 63 | Roger Moore | 39 | 2018-2022 | |
| 63 | Dave Myers | 39 | 2015-2019 | |
| 63 | Cisco Ortega# | 39 | 2024-2027 | |
| 63 | Nathan Phillips | 39 | 2018-2022 | |
| 63 | Edward Schmitt | 39 | 2016-2020 | |
| 63 | Ludovico Turco | 39 | 2016-2020 | |
| 63 | Don Wright | 39 | 2018-2022 | |
| 76 | Tony Austin | 38 | 2013-2018 | |
| 76 | Lawrence Draper | 38 | 2018-2022 | |
| 76 | Anastasio Franco | 38 | 2016-2021 | |
| 76 | Brian Garnham# | 38 | 2024-2027 | |
| 76 | George Jenkins | 38 | 2015-2019 | |
| 76 | Marlon Jennings | 38 | 2016-2020 | |
| 76 | John Lannan | 38 | 2004-2007 | |
| 76 | Juan López | 38 | 2015-2019 | |
| 76 | Chet Miller | 38 | 2016-2020 | |
| 76 | Ben Morgan | 38 | 2014-2018 | |
| 76 | Micah Olson# | 38 | 2013-2014 | |
| 76 | Samuel Parrish# | 38 | 2024-2027 | |
| 76 | Logan Roberts | 38 | 2012-2017 | |
| 76 | Jorge Romero | 38 | 2015-2019 | |
| 76 | José Toro# | 38 | 2025-2028 | |
| 76 | Alberto Torres | 38 | 2018-2021 | |
| 76 | Dave Watson | 38 | 2016-2020 | |
| 76 | Ioachime Zasyadko | 38 | 2018-2022 | |
| 76 | Júlio Zumaya# | 38 | 2024-2027 | |
| 95 | Jorge García# | 37 | 2022-2024 | |
| 95 | Michael Gilman | 37 | 2016-2021 | |
| 95 | Carlos Guillén | 37 | 2022-2024 | |
| 95 | Martin Hamilton | 37 | 2018-2022 | |
| 95 | Joe Johnson# | 37 | 2025-2028 | |
| 95 | Gwon-beom Kim | 37 | 2022-2024 |
