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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 | Bob Hill | 25 | 2016-2019 | |
| 4 | Ed Armstrong# | 24 | 2016-2019 | |
| 4 | Howard Poole | 24 | 2016-2019 | |
| 6 | Jason Davis | 22 | 2015-2018 | |
| 6 | Eliot Moreau# | 22 | 2018-2021 | |
| 6 | Cliff Smith | 22 | 2012-2016 | |
| 6 | Rob Young | 22 | 2012-2015 | |
| 10 | Eric Edwards | 21 | 2016-2019 | |
| 10 | Jon Morris | 21 | 2015-2018 | |
| 10 | Michael Moyer# | 21 | 2018-2021 | |
| 10 | Tom O'Day# | 21 | 2012-2016 | |
| 10 | John Stroud# | 21 | 2017-2020 | |
| 10 | Ray Weeks | 21 | 2016-2019 | |
| 10 | Dylan Wilson# | 21 | 2022-2025 | |
| 17 | Jude Anderson | 20 | 2016-2019 | |
| 17 | William Howard | 20 | 2012-2015 | |
| 17 | Kevin Landry | 20 | 2012-2015 | |
| 17 | António Navarro# | 20 | 2016-2019 | |
| 17 | Bryan Peterson | 20 | 2012-2016 | |
| 17 | Jake Robinson | 20 | 2012-2016 | |
| 23 | Will Caron# | 19 | 2018-2021 | |
| 23 | Rod Crowe | 19 | 2015-2018 | |
| 23 | Carlos Díaz | 19 | 2012-2015 | |
| 23 | Stephen Harding | 19 | 2016-2019 | |
| 23 | Chris Hastings | 19 | 2017-2020 | |
| 23 | John Jones | 19 | 2012-2016 | |
| 23 | Jorge López | 19 | 2018-2021 | |
| 23 | Bob Moore | 19 | 2012-2015 | |
| 23 | Félix Ortíz | 19 | 2012-2015 | |
| 23 | Gustavo Sánchez | 19 | 2016-2019 | |
| 23 | John Slater | 19 | 2014-2017 | |
| 23 | Tim Walker | 19 | 2017-2019 | |
| 35 | Tommy Bartlett | 18 | 2015-2018 | |
| 35 | Nate Chapman# | 18 | 2022-2024 | |
| 35 | Pedro Díaz | 18 | 2012-2016 | |
| 35 | David Duarte# | 18 | 2023-2025 | |
| 35 | Jesús Feliciano | 18 | 2012-2015 | |
| 35 | Luis Fuentes | 18 | 2012-2014 | |
| 35 | Christian Harris | 18 | 2013-2016 | |
| 35 | Ruberto Laranjeira | 18 | 2017-2020 | |
| 35 | Ed Lott | 18 | 2012-2015 | |
| 35 | Anthony McIntyre# | 18 | 2017-2020 | |
| 35 | Juan Mendoza | 18 | 2012-2015 | |
| 35 | Fred Price# | 18 | 2021-2023 | |
| 35 | Pancho Romero | 18 | 2012-2014 | |
| 35 | Carlos Ruíz | 18 | 2012-2015 | |
| 35 | Armando Zavagoza | 18 | 2016-2019 | |
| 50 | Troy Davis | 17 | 2012-2016 | |
| 50 | José Delgado | 17 | 2012-2015 | |
| 50 | Robinson García | 17 | 2012-2016 | |
| 50 | Jorge Hernández | 17 | 2012-2014 | |
| 50 | Paul Johnston# | 17 | 2022-2024 | |
| 50 | Ken Lutz | 17 | 2017-2020 | |
| 50 | Jonathan Martin# | 17 | 2012-2015 | |
| 50 | Joël Mastroianni | 17 | 2012-2014 | |
| 50 | James Phillips | 17 | 2012-2014 | |
| 50 | River Reid | 17 | 2022-2024 | |
| 50 | Pancho Soriano | 17 | 2026-2029 | |
| 50 | Richard Stevenson | 17 | 2012-2015 | |
| 50 | Bubba Thompson | 17 | 2012-2015 | |
| 50 | Paul Wise | 17 | 2016-2019 | |
| 64 | Tony Baltiérrez | 16 | 2015-2018 | |
| 64 | Tomás Bravo# | 16 | 2019-2021 | |
| 64 | Mike Bunch# | 16 | 2025-2027 | |
| 64 | John Cannon | 16 | 2013-2016 | |
| 64 | Jonathan Clark | 16 | 2015-2018 | |
| 64 | Theodore Foster | 16 | 2012-2015 | |
| 64 | Chris Johnson | 16 | 2018-2021 | |
| 64 | Paul Johnston | 16 | 2012-2013 | |
| 64 | Hugh Martin | 16 | 2017-2020 | |
| 64 | David Myers# | 16 | 2025-2027 | |
| 64 | Jesús Ortíz | 16 | 2012-2016 | |
| 64 | Curt Rhodes | 16 | 2012-2015 | |
| 64 | Brad Rodgers | 16 | 2017-2020 | |
| 64 | Oliver Romero# | 16 | 2019-2021 | |
| 64 | Fabián Torres | 16 | 2012-2014 | |
| 64 | Julián Vázquez | 16 | 2022-2024 | |
| 64 | David White | 16 | 2012-2014 | |
| 64 | Buddy Wills | 16 | 2012-2013 | |
| 82 | Jason Adams | 15 | 2012-2014 | |
| 82 | Jeffrey Allison | 15 | 2015-2018 | |
| 82 | Bernard Antoine | 15 | 2018-2020 | |
| 82 | Jason Atkinson | 15 | 2019-2021 | |
| 82 | Eric Billings | 15 | 2015-2018 | |
| 82 | Román Cruz | 15 | 2016-2018 | |
| 82 | Gerardo Estrada# | 15 | 2019-2021 | |
| 82 | Jason Foster | 15 | 2016-2018 | |
| 82 | Alberto García# | 15 | 2026-2028 | |
| 82 | Alexis Garrett# | 15 | 2019-2021 | |
| 82 | Bill George | 15 | 2016-2019 | |
| 82 | Pat Glass# | 15 | 2027-2029 | |
| 82 | Lewis Hunter | 15 | 2014-2017 | |
| 82 | Rob MacKinney | 15 | 2021-2023 | |
| 82 | Marcos Marino# | 15 | 2021-2023 | |
| 82 | Luis Martínez | 15 | 2016-2019 | |
| 82 | Gabriel Núñez# | 15 | 2018-2021 | |
| 82 | Arturo Salinas | 15 | 2018-2021 | |
| 82 | Ben Savage | 15 | 2016-2019 |
