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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jeff Hale | 81 | 2014-2027 | |
| 2 | Nathaniel Riley# | 80 | 2016-2029 | |
| 3 | Nicholas Wells# | 76 | 2019-2029 | |
| 4 | Javier Mora# | 63 | 2020-2029 | |
| 5 | Bartolomeu Lio# | 62 | 2019-2029 | |
| 5 | Pedro Valdéz# | 62 | 2020-2029 | |
| 7 | Héctor Alarcon# | 57 | 2015-2027 | |
| 7 | Paul Díaz# | 57 | 2019-2029 | |
| 9 | Wayne Craig# | 56 | 2015-2023 | |
| 10 | Allen Yohemas# | 55 | 2022-2029 | |
| 11 | Andy Coker | 54 | 2016-2026 | |
| 11 | Wayne Hurst | 54 | 2015-2028 | |
| 13 | Rafael Cardona# | 50 | 2022-2029 | |
| 13 | Wes Hamm# | 50 | 2021-2027 | |
| 15 | Pedro Castro# | 49 | 2018-2029 | |
| 15 | Eddie Kop# | 49 | 2023-2028 | |
| 17 | Chip Bishop# | 48 | 2018-2028 | |
| 17 | John Wilkins# | 48 | 2015-2026 | |
| 19 | Robbie Baxter# | 47 | 2022-2029 | |
| 20 | John Braun | 46 | 2014-2022 | |
| 20 | John Holley | 46 | 2014-2022 | |
| 20 | Roderick Rhodes# | 46 | 2017-2028 | |
| 23 | Bobby Swain# | 45 | 2020-2028 | |
| 24 | Aurelio López# | 43 | 2022-2027 | |
| 25 | Arnie Pittman# | 42 | 2022-2029 | |
| 26 | Allen Blair# | 41 | 2015-2028 | |
| 27 | Domingo Ramírez# | 40 | 2022-2029 | |
| 28 | Henry Hall# | 39 | 2015-2026 | |
| 29 | Michael Battle | 38 | 2017-2021 | |
| 29 | Guillermo Pérez | 38 | 2015-2025 | |
| 31 | Pat Horton | 37 | 2014-2019 | |
| 32 | Juan Guillén# | 36 | 2027-2029 | |
| 32 | Tyler MacHugh# | 36 | 2023-2029 | |
| 34 | Ricardo Hernández | 35 | 2014-2018 | |
| 34 | Félix Jiménez# | 35 | 2018-2028 | |
| 34 | Truman Valentine# | 35 | 2022-2029 | |
| 34 | Benny York# | 35 | 2016-2027 | |
| 38 | Gavin Blackburn# | 34 | 2017-2026 | |
| 39 | Gary Bailey# | 33 | 2022-2026 | |
| 39 | Juan Díaz# | 33 | 2025-2029 | |
| 39 | Roger Garrett | 33 | 2014-2024 | |
| 39 | Lou Hartling# | 33 | 2019-2027 | |
| 39 | Francisco Valdés# | 33 | 2022-2029 | |
| 39 | Hunter Wilson# | 33 | 2019-2029 | |
| 45 | Manny Caraballo# | 32 | 2022-2028 | |
| 45 | Lynwood Matos# | 32 | 2021-2029 | |
| 45 | Drake Montgomery | 32 | 2015-2020 | |
| 45 | Cory Sanders# | 32 | 2021-2029 | |
| 45 | Decheng Sun | 32 | 2018-2028 | |
| 50 | Adrián Fierro# | 31 | 2017-2029 | |
| 50 | Rich Hunter | 31 | 2014-2021 | |
| 50 | António Marés# | 31 | 2024-2029 | |
| 50 | Aaron Wise# | 31 | 2019-2029 | |
| 54 | Leslie Brooks# | 30 | 2019-2028 | |
| 54 | Ji Jing# | 30 | 2027-2029 | |
| 56 | Kirby Brown# | 29 | 2014-2025 | |
| 56 | Brandeis Vogt# | 29 | 2022-2028 | |
| 58 | Timothy Allen | 28 | 2014-2017 | |
| 58 | Jon Dunn# | 28 | 2024-2029 | |
| 58 | Joe Ellis | 28 | 2016-2021 | |
| 58 | Cole Hall | 28 | 2016-2027 | |
| 58 | Devin Hinton | 28 | 2015-2025 | |
| 58 | Germán Rodríguez# | 28 | 2025-2029 | |
| 58 | Ron Stone# | 28 | 2024-2028 | |
| 65 | Domingo Álvarez# | 27 | 2022-2029 | |
| 65 | Walt Johnston | 27 | 2014-2019 | |
| 65 | Juan Carlos Maestas | 27 | 2016-2021 | |
| 65 | Francis McBride# | 27 | 2023-2027 | |
| 65 | Ilie Paunescu# | 27 | 2017-2029 | |
| 65 | César Vatgos | 27 | 2017-2021 | |
| 71 | Vincent Hall# | 26 | 2021-2029 | |
| 71 | Harris Howard | 26 | 2014-2017 | |
| 71 | Ralph McKinney# | 26 | 2019-2028 | |
| 71 | Cris Mendoza# | 26 | 2017-2029 | |
| 71 | Will Savage | 26 | 2017-2024 | |
| 71 | Richard Sykes | 26 | 2020-2027 | |
| 71 | Luis Torres# | 26 | 2024-2029 | |
| 78 | Pablo De La Torre# | 25 | 2022-2028 | |
| 78 | Albert Emery# | 25 | 2016-2026 | |
| 78 | George Frazier# | 25 | 2017-2029 | |
| 78 | Scott William# | 25 | 2023-2027 | |
| 82 | José Alaniz# | 24 | 2020-2029 | |
| 82 | José García# | 24 | 2023-2028 | |
| 82 | Natalino Golaio# | 24 | 2022-2027 | |
| 82 | Myron Johnson | 24 | 2014-2019 | |
| 82 | Ryoichi Maruyama | 24 | 2015-2027 | |
| 82 | Luis Miguel Rojas | 24 | 2016-2023 | |
| 82 | Felipe Velázquez | 24 | 2017-2022 | |
| 82 | Matt Webber# | 24 | 2021-2028 | |
| 90 | Pedro Alejándrez# | 23 | 2022-2024 | |
| 90 | David Collingwood# | 23 | 2019-2028 | |
| 90 | Bill Fletcher# | 23 | 2019-2028 | |
| 90 | Manuel Garza | 23 | 2015-2020 | |
| 90 | David Hudson# | 23 | 2022-2027 | |
| 90 | Joe Kehoe# | 23 | 2020-2027 | |
| 90 | Francisco López# | 23 | 2020-2027 | |
| 90 | Christian Pitts | 23 | 2017-2025 | |
| 90 | Byron Rogers | 23 | 2015-2021 | |
| 90 | Carl Snyder | 23 | 2016-2021 | |
| 90 | Don Thompson | 23 | 2017-2020 |
