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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# | 79 | 2019-2032 | |
| 3 | Nicholas Wells# | 79 | 2019-2032 | |
| 5 | Rafael Cardona# | 65 | 2022-2032 | |
| 6 | Javier Mora# | 63 | 2020-2031 | |
| 7 | Pedro Valdéz# | 62 | 2020-2031 | |
| 8 | Robbie Baxter# | 58 | 2022-2032 | |
| 8 | Eddie Kop# | 58 | 2023-2032 | |
| 10 | Héctor Alarcon# | 57 | 2015-2027 | |
| 10 | Paul Díaz | 57 | 2019-2030 | |
| 12 | Wayne Craig | 56 | 2015-2023 | |
| 13 | Allen Yohemas# | 55 | 2022-2031 | |
| 14 | Andy Coker | 54 | 2016-2026 | |
| 14 | Juan Guillén# | 54 | 2027-2030 | |
| 14 | Wayne Hurst | 54 | 2015-2028 | |
| 17 | Wes Hamm# | 50 | 2021-2027 | |
| 18 | Pedro Castro# | 49 | 2018-2032 | |
| 19 | Chip Bishop | 48 | 2018-2028 | |
| 19 | Allen Blair# | 48 | 2015-2032 | |
| 19 | Bobby Swain# | 48 | 2020-2031 | |
| 19 | John Wilkins | 48 | 2015-2026 | |
| 23 | John Braun | 46 | 2014-2022 | |
| 23 | John Holley | 46 | 2014-2022 | |
| 23 | Roderick Rhodes | 46 | 2017-2028 | |
| 26 | Walt Coffman# | 44 | 2026-2032 | |
| 27 | Aurelio López# | 43 | 2022-2031 | |
| 27 | Truman Valentine# | 43 | 2022-2031 | |
| 29 | Vincent Hall# | 42 | 2021-2031 | |
| 29 | Ralph McKinney# | 42 | 2019-2032 | |
| 29 | Arnie Pittman# | 42 | 2022-2030 | |
| 32 | Tyler MacHugh# | 40 | 2023-2032 | |
| 32 | Domingo Ramírez# | 40 | 2022-2030 | |
| 32 | Juan Torres# | 40 | 2021-2032 | |
| 35 | Henry Hall | 39 | 2015-2026 | |
| 36 | Michael Battle | 38 | 2017-2021 | |
| 36 | Lynwood Matos# | 38 | 2021-2031 | |
| 36 | Guillermo Pérez | 38 | 2015-2025 | |
| 36 | Luis Torres# | 38 | 2024-2031 | |
| 40 | Pat Horton | 37 | 2014-2019 | |
| 41 | António Marés# | 36 | 2024-2031 | |
| 42 | Ricardo Hernández | 35 | 2014-2018 | |
| 42 | Félix Jiménez | 35 | 2018-2028 | |
| 42 | Rafael Rodríguez# | 35 | 2026-2031 | |
| 42 | Hunter Wilson | 35 | 2019-2031 | |
| 42 | Benny York | 35 | 2016-2027 | |
| 47 | Gavin Blackburn | 34 | 2017-2032 | |
| 47 | Germán Rodríguez# | 34 | 2025-2031 | |
| 49 | Gary Bailey | 33 | 2022-2031 | |
| 49 | Juan Díaz# | 33 | 2025-2030 | |
| 49 | Roger Garrett | 33 | 2014-2024 | |
| 49 | Lou Hartling | 33 | 2019-2030 | |
| 49 | Keisuke Nishida# | 33 | 2027-2032 | |
| 49 | Francisco Valdés# | 33 | 2022-2029 | |
| 55 | Manny Caraballo# | 32 | 2022-2028 | |
| 55 | Jon Dunn# | 32 | 2024-2032 | |
| 55 | Drake Montgomery | 32 | 2015-2020 | |
| 55 | Javier Roldán# | 32 | 2025-2032 | |
| 55 | Cory Sanders# | 32 | 2021-2031 | |
| 55 | Decheng Sun | 32 | 2018-2028 | |
| 61 | Adrián Fierro# | 31 | 2017-2032 | |
| 61 | Rich Hunter | 31 | 2014-2021 | |
| 61 | Aaron Wise | 31 | 2019-2029 | |
| 64 | Leslie Brooks | 30 | 2019-2030 | |
| 64 | Ji Jing# | 30 | 2027-2029 | |
| 64 | Rafael Rivera# | 30 | 2027-2032 | |
| 67 | Art Adams# | 29 | 2020-2031 | |
| 67 | Kirby Brown | 29 | 2014-2030 | |
| 67 | George Frazier# | 29 | 2017-2031 | |
| 67 | Ilie Paunescu# | 29 | 2017-2032 | |
| 67 | Gustavo Pérez# | 29 | 2027-2032 | |
| 67 | Brandeis Vogt# | 29 | 2022-2030 | |
| 73 | Timothy Allen | 28 | 2014-2017 | |
| 73 | Joe Ellis | 28 | 2016-2021 | |
| 73 | Cole Hall | 28 | 2016-2027 | |
| 73 | Devin Hinton | 28 | 2015-2025 | |
| 73 | Ash Ibarra# | 28 | 2029-2032 | |
| 73 | Ron Stone# | 28 | 2024-2031 | |
| 73 | Scott William# | 28 | 2023-2032 | |
| 73 | Alfonso Zapata# | 28 | 2020-2032 | |
| 81 | Domingo Álvarez# | 27 | 2022-2029 | |
| 81 | Walt Johnston | 27 | 2014-2019 | |
| 81 | Juan Carlos Maestas | 27 | 2016-2021 | |
| 81 | Francis McBride# | 27 | 2023-2027 | |
| 81 | César Vatgos | 27 | 2017-2021 | |
| 86 | Harris Howard | 26 | 2014-2017 | |
| 86 | Cris Mendoza | 26 | 2017-2029 | |
| 86 | Will Savage | 26 | 2017-2024 | |
| 86 | Richard Sykes | 26 | 2020-2027 | |
| 86 | Bill Tugwell# | 26 | 2029-2032 | |
| 91 | Pablo De La Torre# | 25 | 2022-2028 | |
| 91 | Albert Emery | 25 | 2016-2026 | |
| 91 | Stanley Yelnats# | 25 | 2030-2032 | |
| 94 | José Alaniz# | 24 | 2020-2030 | |
| 94 | José García# | 24 | 2023-2028 | |
| 94 | Natalino Golaio# | 24 | 2022-2031 | |
| 94 | Myron Johnson | 24 | 2014-2019 | |
| 94 | Ryoichi Maruyama | 24 | 2015-2027 | |
| 94 | Luis Miguel Rojas | 24 | 2016-2023 | |
| 94 | Dave Turner# | 24 | 2026-2032 |
