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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Juan Guillén | 112 | 2027-2039 | |
| 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 | 2023-2042 | |
| 8 | Gustavo Tobías# | 71 | 2032-2044 | |
| 9 | Pedro Valdéz | 68 | 2020-2040 | |
| 10 | Robbie Baxter | 64 | 2022-2037 | |
| 11 | Javier Mora | 63 | 2020-2034 | |
| 12 | Walt Coffman* | 61 | 2026-2038 | |
| 13 | Wes Hamm* | 60 | 2021-2037 | |
| 14 | Héctor Alarcon | 57 | 2015-2027 | |
| 14 | Paul Díaz | 57 | 2019-2030 | |
| 16 | Wayne Craig | 56 | 2015-2023 | |
| 17 | Jesús Vidro# | 55 | 2033-2044 | |
| 17 | Allen Yohemas | 55 | 2022-2031 | |
| 19 | Andy Coker | 54 | 2016-2026 | |
| 19 | Wayne Hurst | 54 | 2015-2028 | |
| 21 | Anastasio Cabanillas Jr.# | 53 | 2037-2044 | |
| 21 | David Moore# | 53 | 2034-2043 | |
| 21 | Domingo Ramírez | 53 | 2022-2039 | |
| 24 | Matthew Fallows# | 52 | 2034-2044 | |
| 24 | Travis Morgan# | 52 | 2039-2044 | |
| 26 | Pedro Castro | 49 | 2018-2032 | |
| 26 | Stanford McCain | 49 | 2031-2041 | |
| 28 | Chip Bishop | 48 | 2018-2028 | |
| 28 | Allen Blair | 48 | 2015-2032 | |
| 28 | Tyler MacHugh | 48 | 2023-2033 | |
| 28 | Juan Moreno# | 48 | 2037-2044 | |
| 28 | Bobby Swain | 48 | 2020-2031 | |
| 28 | John Wilkins* | 48 | 2015-2026 | |
| 28 | Stanley Yelnats | 48 | 2030-2038 | |
| 35 | John Braun | 46 | 2014-2022 | |
| 35 | John Holley | 46 | 2014-2022 | |
| 35 | Roderick Rhodes | 46 | 2017-2028 | |
| 38 | Anatoly Ivanovich | 45 | 2030-2039 | |
| 38 | Aurelio López | 45 | 2022-2037 | |
| 40 | Zhao-ji Qiu# | 44 | 2036-2044 | |
| 41 | Truman Valentine | 43 | 2022-2031 | |
| 42 | Faisal bin Nabeel | 42 | 2034-2041 | |
| 42 | Ratko Davidovic# | 42 | 2035-2043 | |
| 42 | Juan Díaz | 42 | 2025-2036 | |
| 42 | Vincent Hall | 42 | 2021-2031 | |
| 42 | Ralph McKinney* | 42 | 2019-2034 | |
| 42 | Arnie Pittman | 42 | 2022-2030 | |
| 48 | Jorge Otero | 41 | 2030-2040 | |
| 49 | Kevin Nogilny# | 40 | 2032-2043 | |
| 49 | Joe Pruitt | 40 | 2031-2039 | |
| 49 | Armando Romano | 40 | 2029-2042 | |
| 49 | Juan Torres | 40 | 2021-2032 | |
| 53 | Urs Ehles# | 39 | 2036-2044 | |
| 53 | Henry Hall | 39 | 2015-2026 | |
| 53 | Luis Torres | 39 | 2024-2035 | |
| 56 | Michael Battle | 38 | 2017-2021 | |
| 56 | George Frazier | 38 | 2017-2036 | |
| 56 | Paul Haines# | 38 | 2038-2044 | |
| 56 | Kyuichi Hori# | 38 | 2031-2042 | |
| 56 | Ton Jobse# | 38 | 2031-2037 | |
| 56 | Lynwood Matos | 38 | 2021-2031 | |
| 56 | Guillermo Pérez | 38 | 2015-2025 | |
| 63 | Dave Becker# | 37 | 2040-2044 | |
| 63 | Jong-yong Ha# | 37 | 2038-2044 | |
| 63 | Van Hileman# | 37 | 2041-2044 | |
| 63 | Pat Horton | 37 | 2014-2019 | |
| 63 | Roger Rodenburg# | 37 | 2036-2044 | |
| 63 | Cory Sanders | 37 | 2021-2036 | |
| 63 | Brantford Winstworth III# | 37 | 2029-2043 | |
| 70 | Chris Holland# | 36 | 2035-2044 | |
| 70 | António Marés | 36 | 2024-2031 | |
| 70 | António Muñóz | 36 | 2029-2039 | |
| 73 | Gary Ashley# | 35 | 2034-2044 | |
| 73 | Manuel Delgadillo | 35 | 2028-2038 | |
| 73 | Ricardo Hernández | 35 | 2014-2018 | |
| 73 | Félix Jiménez | 35 | 2018-2028 | |
| 73 | Raúl Luna | 35 | 2028-2036 | |
| 73 | José Quiñones | 35 | 2034-2043 | |
| 73 | Rafael Rodríguez | 35 | 2026-2031 | |
| 73 | Hunter Wilson | 35 | 2019-2031 | |
| 73 | Benny York | 35 | 2016-2027 | |
| 82 | Gavin Blackburn | 34 | 2017-2032 | |
| 82 | Pablo De La Torre | 34 | 2022-2036 | |
| 82 | Maru Pao Pao | 34 | 2029-2037 | |
| 82 | Rafael Rivera | 34 | 2027-2039 | |
| 82 | Germán Rodríguez | 34 | 2025-2040 | |
| 82 | Brandeis Vogt | 34 | 2022-2036 | |
| 88 | Gary Bailey* | 33 | 2022-2031 | |
| 88 | Ralph DePalma# | 33 | 2036-2044 | |
| 88 | Jon Dunn | 33 | 2024-2034 | |
| 88 | Roger Garrett | 33 | 2014-2024 | |
| 88 | Lou Hartling | 33 | 2019-2030 | |
| 88 | Nelle Liefting | 33 | 2022-2036 | |
| 88 | Michael Machen | 33 | 2029-2041 | |
| 88 | Keisuke Nishida | 33 | 2027-2032 | |
| 88 | Elroy Quaid# | 33 | 2036-2044 | |
| 88 | Francisco Valdés | 33 | 2022-2033 | |
| 98 | Manny Caraballo | 32 | 2022-2028 | |
| 98 | Zaki Fakhiri# | 32 | 2034-2042 | |
| 98 | Ji Jing | 32 | 2027-2035 |
