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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Nathaniel Riley# | 85 | 2016-2030 | |
| 2 | Jeff Hale | 81 | 2014-2027 | |
| 3 | Nicholas Wells# | 76 | 2019-2029 | |
| 4 | Bartolomeu Lio# | 65 | 2019-2030 | |
| 5 | Javier Mora# | 63 | 2020-2030 | |
| 6 | Pedro Valdéz# | 62 | 2020-2029 | |
| 7 | Héctor Alarcon# | 57 | 2015-2027 | |
| 7 | Paul Díaz# | 57 | 2019-2030 | |
| 9 | Wayne Craig# | 56 | 2015-2023 | |
| 10 | Rafael Cardona# | 55 | 2022-2030 | |
| 10 | Allen Yohemas# | 55 | 2022-2030 | |
| 12 | Andy Coker | 54 | 2016-2026 | |
| 12 | Juan Guillén# | 54 | 2027-2030 | |
| 12 | Wayne Hurst | 54 | 2015-2028 | |
| 15 | Robbie Baxter# | 53 | 2022-2030 | |
| 16 | Wes Hamm# | 50 | 2021-2027 | |
| 17 | Pedro Castro# | 49 | 2018-2029 | |
| 17 | Eddie Kop# | 49 | 2023-2030 | |
| 19 | Chip Bishop# | 48 | 2018-2028 | |
| 19 | John Wilkins | 48 | 2015-2026 | |
| 21 | John Braun | 46 | 2014-2022 | |
| 21 | John Holley | 46 | 2014-2022 | |
| 21 | Roderick Rhodes | 46 | 2017-2028 | |
| 21 | Bobby Swain# | 46 | 2020-2030 | |
| 25 | Aurelio López# | 43 | 2022-2030 | |
| 26 | Arnie Pittman# | 42 | 2022-2030 | |
| 27 | Allen Blair# | 41 | 2015-2030 | |
| 27 | Truman Valentine# | 41 | 2022-2030 | |
| 29 | Tyler MacHugh# | 40 | 2023-2030 | |
| 29 | Domingo Ramírez# | 40 | 2022-2030 | |
| 31 | Henry Hall | 39 | 2015-2026 | |
| 32 | Michael Battle | 38 | 2017-2021 | |
| 32 | Guillermo Pérez | 38 | 2015-2025 | |
| 34 | Pat Horton | 37 | 2014-2019 | |
| 35 | Ralph McKinney# | 36 | 2019-2030 | |
| 36 | Ricardo Hernández | 35 | 2014-2018 | |
| 36 | Félix Jiménez | 35 | 2018-2028 | |
| 36 | Benny York | 35 | 2016-2027 | |
| 39 | Gavin Blackburn# | 34 | 2017-2030 | |
| 39 | Luis Torres# | 34 | 2024-2030 | |
| 41 | Gary Bailey# | 33 | 2022-2030 | |
| 41 | Juan Díaz# | 33 | 2025-2030 | |
| 41 | Roger Garrett | 33 | 2014-2024 | |
| 41 | Vincent Hall# | 33 | 2021-2030 | |
| 41 | Lou Hartling# | 33 | 2019-2030 | |
| 41 | Lynwood Matos# | 33 | 2021-2030 | |
| 41 | Francisco Valdés# | 33 | 2022-2029 | |
| 41 | Hunter Wilson# | 33 | 2019-2030 | |
| 49 | Manny Caraballo# | 32 | 2022-2028 | |
| 49 | Drake Montgomery | 32 | 2015-2020 | |
| 49 | Cory Sanders# | 32 | 2021-2029 | |
| 49 | Decheng Sun | 32 | 2018-2028 | |
| 53 | Adrián Fierro# | 31 | 2017-2029 | |
| 53 | Rich Hunter | 31 | 2014-2021 | |
| 53 | António Marés# | 31 | 2024-2030 | |
| 53 | Aaron Wise# | 31 | 2019-2029 | |
| 57 | Leslie Brooks# | 30 | 2019-2030 | |
| 57 | Ji Jing# | 30 | 2027-2029 | |
| 57 | Juan Torres# | 30 | 2021-2030 | |
| 60 | Kirby Brown | 29 | 2014-2030 | |
| 60 | George Frazier# | 29 | 2017-2030 | |
| 60 | Brandeis Vogt# | 29 | 2022-2030 | |
| 63 | Timothy Allen | 28 | 2014-2017 | |
| 63 | Jon Dunn# | 28 | 2024-2029 | |
| 63 | Joe Ellis | 28 | 2016-2021 | |
| 63 | Cole Hall | 28 | 2016-2027 | |
| 63 | Devin Hinton | 28 | 2015-2025 | |
| 63 | Germán Rodríguez# | 28 | 2025-2030 | |
| 63 | Ron Stone# | 28 | 2024-2028 | |
| 70 | Domingo Álvarez# | 27 | 2022-2029 | |
| 70 | Walt Johnston | 27 | 2014-2019 | |
| 70 | Juan Carlos Maestas | 27 | 2016-2021 | |
| 70 | Francis McBride# | 27 | 2023-2027 | |
| 70 | Ilie Paunescu# | 27 | 2017-2030 | |
| 70 | Gustavo Pérez# | 27 | 2027-2030 | |
| 70 | César Vatgos | 27 | 2017-2021 | |
| 77 | Harris Howard | 26 | 2014-2017 | |
| 77 | Cris Mendoza | 26 | 2017-2029 | |
| 77 | Will Savage | 26 | 2017-2024 | |
| 77 | Richard Sykes | 26 | 2020-2027 | |
| 81 | Pablo De La Torre# | 25 | 2022-2028 | |
| 81 | Albert Emery | 25 | 2016-2026 | |
| 81 | Rafael Rivera# | 25 | 2027-2030 | |
| 81 | Scott William# | 25 | 2023-2027 | |
| 85 | José Alaniz# | 24 | 2020-2030 | |
| 85 | José García# | 24 | 2023-2028 | |
| 85 | Natalino Golaio# | 24 | 2022-2030 | |
| 85 | Myron Johnson | 24 | 2014-2019 | |
| 85 | Ryoichi Maruyama | 24 | 2015-2027 | |
| 85 | Luis Miguel Rojas | 24 | 2016-2023 | |
| 85 | Dave Turner# | 24 | 2026-2030 | |
| 85 | Felipe Velázquez | 24 | 2017-2022 | |
| 85 | Matt Webber# | 24 | 2021-2028 | |
| 94 | Pedro Alejándrez# | 23 | 2022-2030 | |
| 94 | David Collingwood# | 23 | 2019-2028 | |
| 94 | Bill Fletcher | 23 | 2019-2028 | |
| 94 | Manuel Garza | 23 | 2015-2020 | |
| 94 | David Hudson# | 23 | 2022-2027 | |
| 94 | Joe Kehoe# | 23 | 2020-2027 | |
| 94 | Francisco López# | 23 | 2020-2027 |
