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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 | Bartolomeu Lio# | 76 | 2019-2031 | |
| 3 | Nicholas Wells# | 76 | 2019-2029 | |
| 5 | Javier Mora# | 63 | 2020-2031 | |
| 6 | Pedro Valdéz# | 62 | 2020-2031 | |
| 7 | Robbie Baxter# | 58 | 2022-2031 | |
| 8 | Héctor Alarcon# | 57 | 2015-2027 | |
| 8 | Paul Díaz | 57 | 2019-2030 | |
| 10 | Wayne Craig# | 56 | 2015-2023 | |
| 11 | Rafael Cardona# | 55 | 2022-2030 | |
| 11 | Allen Yohemas# | 55 | 2022-2031 | |
| 13 | Andy Coker | 54 | 2016-2026 | |
| 13 | Juan Guillén# | 54 | 2027-2030 | |
| 13 | Wayne Hurst | 54 | 2015-2028 | |
| 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 | Bobby Swain# | 48 | 2020-2031 | |
| 19 | John Wilkins | 48 | 2015-2026 | |
| 22 | John Braun | 46 | 2014-2022 | |
| 22 | John Holley | 46 | 2014-2022 | |
| 22 | Roderick Rhodes | 46 | 2017-2028 | |
| 25 | Aurelio López# | 43 | 2022-2031 | |
| 25 | Truman Valentine# | 43 | 2022-2031 | |
| 27 | Vincent Hall# | 42 | 2021-2031 | |
| 27 | Ralph McKinney# | 42 | 2019-2031 | |
| 27 | Arnie Pittman# | 42 | 2022-2030 | |
| 30 | Allen Blair# | 41 | 2015-2031 | |
| 31 | Tyler MacHugh# | 40 | 2023-2031 | |
| 31 | Domingo Ramírez# | 40 | 2022-2030 | |
| 33 | Henry Hall | 39 | 2015-2026 | |
| 33 | Juan Torres# | 39 | 2021-2031 | |
| 35 | Michael Battle | 38 | 2017-2021 | |
| 35 | Lynwood Matos# | 38 | 2021-2031 | |
| 35 | Guillermo Pérez | 38 | 2015-2025 | |
| 35 | Luis Torres# | 38 | 2024-2031 | |
| 39 | Pat Horton | 37 | 2014-2019 | |
| 40 | António Marés# | 36 | 2024-2031 | |
| 41 | Ricardo Hernández | 35 | 2014-2018 | |
| 41 | Félix Jiménez | 35 | 2018-2028 | |
| 41 | Rafael Rodríguez# | 35 | 2026-2031 | |
| 41 | Hunter Wilson# | 35 | 2019-2031 | |
| 41 | Benny York | 35 | 2016-2027 | |
| 46 | Gavin Blackburn# | 34 | 2017-2031 | |
| 46 | Germán Rodríguez# | 34 | 2025-2031 | |
| 48 | Gary Bailey# | 33 | 2022-2031 | |
| 48 | Juan Díaz# | 33 | 2025-2030 | |
| 48 | Roger Garrett | 33 | 2014-2024 | |
| 48 | Lou Hartling | 33 | 2019-2030 | |
| 48 | Francisco Valdés# | 33 | 2022-2029 | |
| 53 | Manny Caraballo# | 32 | 2022-2028 | |
| 53 | Drake Montgomery | 32 | 2015-2020 | |
| 53 | Cory Sanders# | 32 | 2021-2031 | |
| 53 | Decheng Sun | 32 | 2018-2028 | |
| 57 | Walt Coffman# | 31 | 2026-2031 | |
| 57 | Adrián Fierro# | 31 | 2017-2031 | |
| 57 | Rich Hunter | 31 | 2014-2021 | |
| 57 | Aaron Wise# | 31 | 2019-2029 | |
| 61 | Leslie Brooks# | 30 | 2019-2030 | |
| 61 | Ji Jing# | 30 | 2027-2029 | |
| 61 | Rafael Rivera# | 30 | 2027-2031 | |
| 64 | Art Adams# | 29 | 2020-2031 | |
| 64 | Kirby Brown | 29 | 2014-2030 | |
| 64 | George Frazier# | 29 | 2017-2031 | |
| 64 | Brandeis Vogt# | 29 | 2022-2030 | |
| 68 | Timothy Allen | 28 | 2014-2017 | |
| 68 | Jon Dunn# | 28 | 2024-2031 | |
| 68 | Joe Ellis | 28 | 2016-2021 | |
| 68 | Cole Hall | 28 | 2016-2027 | |
| 68 | Devin Hinton | 28 | 2015-2025 | |
| 68 | Ron Stone# | 28 | 2024-2031 | |
| 74 | Domingo Álvarez# | 27 | 2022-2029 | |
| 74 | Walt Johnston | 27 | 2014-2019 | |
| 74 | Juan Carlos Maestas | 27 | 2016-2021 | |
| 74 | Francis McBride# | 27 | 2023-2027 | |
| 74 | Ilie Paunescu# | 27 | 2017-2030 | |
| 74 | Gustavo Pérez# | 27 | 2027-2030 | |
| 74 | César Vatgos | 27 | 2017-2021 | |
| 81 | Harris Howard | 26 | 2014-2017 | |
| 81 | Cris Mendoza | 26 | 2017-2029 | |
| 81 | Keisuke Nishida# | 26 | 2027-2031 | |
| 81 | Javier Roldán# | 26 | 2025-2031 | |
| 81 | Will Savage | 26 | 2017-2024 | |
| 81 | Richard Sykes | 26 | 2020-2027 | |
| 87 | Pablo De La Torre# | 25 | 2022-2028 | |
| 87 | Albert Emery | 25 | 2016-2026 | |
| 87 | Scott William# | 25 | 2023-2027 | |
| 90 | José Alaniz# | 24 | 2020-2030 | |
| 90 | José García# | 24 | 2023-2028 | |
| 90 | Natalino Golaio# | 24 | 2022-2031 | |
| 90 | Myron Johnson | 24 | 2014-2019 | |
| 90 | Ryoichi Maruyama | 24 | 2015-2027 | |
| 90 | Luis Miguel Rojas | 24 | 2016-2023 | |
| 90 | Dave Turner# | 24 | 2026-2030 | |
| 90 | Felipe Velázquez | 24 | 2017-2022 | |
| 90 | Matt Webber | 24 | 2021-2028 | |
| 99 | Pedro Alejándrez# | 23 | 2022-2030 | |
| 99 | David Collingwood# | 23 | 2019-2028 |
