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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Juan Guillén# | 91 | 2027-2036 | |
| 2 | Bartolomeu Lio | 89 | 2019-2034 | |
| 3 | Nathaniel Riley | 85 | 2016-2030 | |
| 4 | Rafael Cardona | 82 | 2022-2035 | |
| 5 | Jeff Hale | 81 | 2014-2027 | |
| 6 | Nicholas Wells | 79 | 2019-2032 | |
| 7 | Eddie Kop# | 74 | 2023-2037 | |
| 8 | Robbie Baxter# | 64 | 2022-2037 | |
| 9 | Javier Mora | 63 | 2020-2034 | |
| 10 | Pedro Valdéz# | 62 | 2020-2037 | |
| 11 | Wes Hamm | 60 | 2021-2037 | |
| 12 | Walt Coffman# | 59 | 2026-2037 | |
| 13 | Héctor Alarcon | 57 | 2015-2027 | |
| 13 | Paul Díaz | 57 | 2019-2030 | |
| 15 | Wayne Craig | 56 | 2015-2023 | |
| 16 | Allen Yohemas | 55 | 2022-2031 | |
| 17 | Andy Coker | 54 | 2016-2026 | |
| 17 | Wayne Hurst | 54 | 2015-2028 | |
| 19 | Domingo Ramírez# | 52 | 2022-2037 | |
| 20 | Pedro Castro | 49 | 2018-2032 | |
| 20 | Stanford McCain# | 49 | 2031-2037 | |
| 22 | Chip Bishop | 48 | 2018-2028 | |
| 22 | Allen Blair | 48 | 2015-2032 | |
| 22 | Tyler MacHugh | 48 | 2023-2033 | |
| 22 | Bobby Swain | 48 | 2020-2031 | |
| 22 | John Wilkins* | 48 | 2015-2026 | |
| 22 | Stanley Yelnats# | 48 | 2030-2036 | |
| 28 | John Braun | 46 | 2014-2022 | |
| 28 | John Holley | 46 | 2014-2022 | |
| 28 | Roderick Rhodes | 46 | 2017-2028 | |
| 31 | Aurelio López# | 45 | 2022-2037 | |
| 32 | Truman Valentine | 43 | 2022-2031 | |
| 33 | Juan Díaz | 42 | 2025-2036 | |
| 33 | Vincent Hall | 42 | 2021-2031 | |
| 33 | Anatoly Ivanovich# | 42 | 2030-2037 | |
| 33 | Ralph McKinney | 42 | 2019-2034 | |
| 33 | Arnie Pittman | 42 | 2022-2030 | |
| 38 | Joe Pruitt# | 40 | 2031-2036 | |
| 38 | Juan Torres | 40 | 2021-2032 | |
| 40 | Henry Hall | 39 | 2015-2026 | |
| 40 | Luis Torres | 39 | 2024-2035 | |
| 42 | Michael Battle | 38 | 2017-2021 | |
| 42 | George Frazier# | 38 | 2017-2036 | |
| 42 | Ton Jobse# | 38 | 2031-2037 | |
| 42 | Lynwood Matos | 38 | 2021-2031 | |
| 42 | Guillermo Pérez | 38 | 2015-2025 | |
| 42 | Jesús Vidro# | 38 | 2033-2037 | |
| 48 | Pat Horton | 37 | 2014-2019 | |
| 48 | Cory Sanders | 37 | 2021-2036 | |
| 50 | António Marés# | 36 | 2024-2031 | |
| 51 | Ricardo Hernández | 35 | 2014-2018 | |
| 51 | Félix Jiménez | 35 | 2018-2028 | |
| 51 | Raúl Luna# | 35 | 2028-2036 | |
| 51 | Rafael Rodríguez | 35 | 2026-2031 | |
| 51 | Hunter Wilson | 35 | 2019-2031 | |
| 51 | Benny York | 35 | 2016-2027 | |
| 57 | Gavin Blackburn | 34 | 2017-2032 | |
| 57 | Pablo De La Torre# | 34 | 2022-2036 | |
| 57 | Matthew Fallows# | 34 | 2034-2037 | |
| 57 | António Muñóz# | 34 | 2029-2037 | |
| 57 | Maru Pao Pao# | 34 | 2029-2037 | |
| 57 | Germán Rodríguez# | 34 | 2025-2031 | |
| 57 | Brandeis Vogt | 34 | 2022-2036 | |
| 64 | Gary Bailey | 33 | 2022-2031 | |
| 64 | Jon Dunn | 33 | 2024-2034 | |
| 64 | Roger Garrett | 33 | 2014-2024 | |
| 64 | Lou Hartling | 33 | 2019-2030 | |
| 64 | Nelle Liefting | 33 | 2022-2036 | |
| 64 | Keisuke Nishida | 33 | 2027-2032 | |
| 64 | Francisco Valdés | 33 | 2022-2033 | |
| 71 | Manny Caraballo | 32 | 2022-2028 | |
| 71 | Ji Jing | 32 | 2027-2035 | |
| 71 | Drake Montgomery | 32 | 2015-2020 | |
| 71 | Javier Roldán | 32 | 2025-2032 | |
| 71 | Decheng Sun | 32 | 2018-2028 | |
| 76 | Adrián Fierro | 31 | 2017-2032 | |
| 76 | Rich Hunter | 31 | 2014-2021 | |
| 76 | Rafael Rivera# | 31 | 2027-2035 | |
| 76 | Rusty Swanson# | 31 | 2025-2037 | |
| 76 | Aaron Wise | 31 | 2019-2029 | |
| 81 | Leslie Brooks | 30 | 2019-2030 | |
| 81 | António Castillo# | 30 | 2026-2037 | |
| 81 | Manuel Delgadillo# | 30 | 2028-2037 | |
| 81 | Carlos Medina# | 30 | 2029-2035 | |
| 85 | Art Adams | 29 | 2020-2031 | |
| 85 | Pedro Alejándrez | 29 | 2022-2034 | |
| 85 | Kirby Brown | 29 | 2014-2030 | |
| 85 | Armando Marrero# | 29 | 2032-2037 | |
| 85 | Ilie Paunescu | 29 | 2017-2032 | |
| 85 | Gustavo Pérez | 29 | 2027-2033 | |
| 91 | Timothy Allen | 28 | 2014-2017 | |
| 91 | Joe Ellis | 28 | 2016-2021 | |
| 91 | Ricardo García# | 28 | 2032-2037 | |
| 91 | Cole Hall | 28 | 2016-2027 | |
| 91 | Devin Hinton | 28 | 2015-2025 | |
| 91 | Ash Ibarra | 28 | 2029-2032 | |
| 91 | Bill Oulton | 28 | 2021-2033 | |
| 91 | Ron Stone | 28 | 2024-2035 | |
| 91 | Scott William | 28 | 2023-2033 | |
| 91 | Alfonso Zapata | 28 | 2020-2032 |
