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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Richard Rogers | 29 | 2012-2016 | |
| 2 | Manuel García | 26 | 2017-2020 | |
| 3 | Ed Armstrong | 24 | 2016-2019 | |
| 3 | Howard Poole | 24 | 2016-2019 | |
| 5 | Jason Davis | 22 | 2015-2018 | |
| 5 | Eliot Moreau | 22 | 2018-2021 | |
| 5 | Rob Young | 22 | 2012-2015 | |
| 8 | Jon Morris | 21 | 2015-2018 | |
| 8 | Michael Moyer | 21 | 2018-2021 | |
| 8 | Tom O'Day | 21 | 2012-2016 | |
| 8 | John Stroud | 21 | 2017-2020 | |
| 8 | Ray Weeks | 21 | 2016-2019 | |
| 8 | Dylan Wilson | 21 | 2022-2025 | |
| 14 | William Howard | 20 | 2012-2015 | |
| 14 | Kevin Landry | 20 | 2012-2015 | |
| 14 | António Navarro | 20 | 2016-2019 | |
| 14 | Jake Robinson | 20 | 2012-2016 | |
| 18 | Will Caron | 19 | 2018-2021 | |
| 18 | Chris Hastings | 19 | 2017-2020 | |
| 18 | John Jones | 19 | 2012-2016 | |
| 18 | Bob Moore | 19 | 2012-2015 | |
| 18 | Félix Ortíz | 19 | 2012-2015 | |
| 18 | John Slater | 19 | 2014-2017 | |
| 18 | Tim Walker | 19 | 2017-2019 | |
| 25 | Tommy Bartlett | 18 | 2015-2018 | |
| 25 | Nate Chapman | 18 | 2022-2024 | |
| 25 | David Duarte | 18 | 2023-2025 | |
| 25 | Pedro Díaz | 18 | 2012-2016 | |
| 25 | Jesús Feliciano | 18 | 2012-2015 | |
| 25 | Luis Fuentes | 18 | 2012-2014 | |
| 25 | Christian Harris | 18 | 2013-2016 | |
| 25 | Ruberto Laranjeira | 18 | 2017-2020 | |
| 25 | Ed Lott | 18 | 2012-2015 | |
| 25 | Anthony McIntyre | 18 | 2017-2020 | |
| 25 | Fred Price | 18 | 2021-2023 | |
| 25 | Pancho Romero | 18 | 2012-2014 | |
| 25 | Carlos Ruíz | 18 | 2012-2015 | |
| 38 | José Delgado | 17 | 2012-2015 | |
| 38 | Robinson García | 17 | 2012-2016 | |
| 38 | Jorge Hernández | 17 | 2012-2014 | |
| 38 | Paul Johnston | 17 | 2022-2024 | |
| 38 | Jonathan Martin | 17 | 2012-2015 | |
| 38 | Joël Mastroianni | 17 | 2012-2014 | |
| 38 | James Phillips | 17 | 2012-2014 | |
| 38 | Paul Wise | 17 | 2016-2019 | |
| 46 | Tony Baltiérrez | 16 | 2015-2018 | |
| 46 | Tomás Bravo* | 16 | 2019-2021 | |
| 46 | John Cannon | 16 | 2013-2016 | |
| 46 | Theodore Foster | 16 | 2012-2015 | |
| 46 | Chris Johnson | 16 | 2018-2021 | |
| 46 | Paul Johnston | 16 | 2012-2013 | |
| 46 | Hugh Martin | 16 | 2017-2020 | |
| 46 | David Myers | 16 | 2025-2027 | |
| 46 | Jesús Ortíz | 16 | 2012-2016 | |
| 46 | Curt Rhodes* | 16 | 2012-2015 | |
| 46 | Oliver Romero | 16 | 2019-2021 | |
| 46 | David White | 16 | 2012-2014 | |
| 46 | Buddy Wills | 16 | 2012-2013 | |
| 59 | Jason Adams | 15 | 2012-2014 | |
| 59 | Gerardo Estrada | 15 | 2019-2021 | |
| 59 | Alberto García | 15 | 2026-2028 | |
| 59 | Alexis Garrett | 15 | 2019-2021 | |
| 59 | Pat Glass | 15 | 2027-2029 | |
| 59 | Lewis Hunter | 15 | 2014-2017 | |
| 59 | Rob MacKinney | 15 | 2021-2023 | |
| 59 | Marcos Marino | 15 | 2021-2023 | |
| 59 | Luis Martínez | 15 | 2016-2019 | |
| 59 | Gabriel Núñez | 15 | 2018-2021 | |
| 59 | Lee Phillips | 15 | 2048-2051 | |
| 59 | Mark Stevenson | 15 | 2015-2018 | |
| 59 | Doug Walsh | 15 | 2012-2014 | |
| 72 | Jim Alt | 14 | 2036-2038 | |
| 72 | Larry Anderson | 14 | 2012-2015 | |
| 72 | Bill Barnes | 14 | 2017-2020 | |
| 72 | Bobby Brabaw | 14 | 2038-2040 | |
| 72 | William Brooks | 14 | 2013-2015 | |
| 72 | Ramón Castaneda | 14 | 2012-2014 | |
| 72 | Robert Cook | 14 | 2020-2021 | |
| 72 | Jeremy Henson# | 14 | 2055-2058 | |
| 72 | Lloyd Huggins | 14 | 2027-2030 | |
| 72 | Kyle Jackson | 14 | 2039-2041 | |
| 72 | Ryan Jenkins | 14 | 2012-2015 | |
| 72 | John Keith | 14 | 2014-2017 | |
| 72 | Eduardo Marino | 14 | 2022-2024 | |
| 72 | Juan Mendoza | 14 | 2018-2019 | |
| 72 | Chuck Noblet | 14 | 2014-2017 | |
| 72 | Jesús Ramírez | 14 | 2012-2015 | |
| 72 | Roger Rogers | 14 | 2025-2027 | |
| 72 | Carlton Shafer | 14 | 2022-2024 | |
| 72 | John Sommerville# | 14 | 2051-2054 | |
| 72 | Ramón Vázquez | 14 | 2012-2014 | |
| 92 | Jason Aves | 13 | 2033-2035 | |
| 92 | Shane Becker | 13 | 2012-2015 | |
| 92 | Fred Butler | 13 | 2012-2014 | |
| 92 | Carl Clay | 13 | 2014-2016 | |
| 92 | Joe Eastwood | 13 | 2042-2044 | |
| 92 | Raúl Flores | 13 | 2022-2024 | |
| 92 | Alexander González | 13 | 2019-2020 | |
| 92 | Todd Green | 13 | 2014-2017 | |
| 92 | Manuel Guerrero | 13 | 2019-2021 |
