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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | José Silva | 68 | 2027-2040 | |
| 2 | Silvio Bolt | 65 | 2026-2037 | |
| 2 | Félix Córdova | 65 | 2023-2035 | |
| 4 | Todd Miller# | 61 | 2036-2040 | |
| 5 | Kitahachi Noda | 59 | 2024-2040 | |
| 5 | Pepe Ramírez# | 59 | 2031-2042 | |
| 7 | Ronald Mitchell# | 58 | 2030-2042 | |
| 8 | Jim Fish | 57 | 2024-2037 | |
| 9 | Barney Swanson# | 54 | 2027-2042 | |
| 10 | Robinson Hernández# | 52 | 2028-2038 | |
| 11 | Joaquín Cerda | 51 | 2028-2040 | |
| 12 | Pedro Torres# | 50 | 2027-2042 | |
| 13 | Andrew Burns | 49 | 2021-2033 | |
| 14 | Adam Pemberton# | 48 | 2027-2040 | |
| 14 | Kikaku Suzuki | 48 | 2022-2030 | |
| 16 | Leonardo González | 47 | 2014-2020 | |
| 17 | Izumo Kondo | 45 | 2025-2031 | |
| 18 | Neil Maes | 44 | 2016-2033 | |
| 19 | José Espinosa# | 43 | 2039-2042 | |
| 20 | Lou Butler# | 42 | 2029-2041 | |
| 20 | Nobuhisa Nagai | 42 | 2017-2031 | |
| 20 | Marcel Osterhout# | 42 | 2029-2040 | |
| 20 | Dylan Stinson# | 42 | 2034-2042 | |
| 24 | Marcos Alcorta | 41 | 2025-2030 | |
| 24 | Júlio Barrera# | 41 | 2037-2042 | |
| 24 | Dan McClain | 41 | 2021-2024 | |
| 24 | Victor McKay | 41 | 2021-2037 | |
| 24 | Ricardo Salazar | 41 | 2011-2018 | |
| 24 | Seong-chae Somun | 41 | 2029-2039 | |
| 30 | Ryan Coyfe# | 40 | 2030-2042 | |
| 30 | Kyoichi Gato | 40 | 2025-2028 | |
| 30 | Pedro Novaro# | 40 | 2027-2038 | |
| 30 | Rafael Quintero | 40 | 2019-2022 | |
| 34 | Matt Allison | 39 | 2019-2032 | |
| 34 | Donald Edwards | 39 | 2015-2023 | |
| 34 | Ángel López# | 39 | 2030-2041 | |
| 34 | Masanobu Ozawa# | 39 | 2040-2042 | |
| 34 | Roberto Rodríguez | 39 | 2028-2039 | |
| 34 | Jesse Strickland | 39 | 2018-2021 | |
| 40 | José Aguilar | 38 | 2017-2029 | |
| 40 | Celestino Corisca | 38 | 2028-2039 | |
| 40 | Luis González# | 38 | 2035-2040 | |
| 40 | José Piña | 38 | 2007-2010 | |
| 44 | Jim Park | 37 | 2012-2017 | |
| 45 | José Casarravias# | 36 | 2037-2042 | |
| 45 | Sebastiaan de Roode# | 36 | 2032-2033 | |
| 45 | Robbie Dupuis | 36 | 2028-2040 | |
| 45 | Juan Garanzuay# | 36 | 2030-2042 | |
| 45 | Tsurayuki Harada | 36 | 2029-2040 | |
| 45 | Zhong-yan Ke# | 36 | 2035-2042 | |
| 45 | Ángel Ramírez | 36 | 2021-2024 | |
| 45 | Norm Wood | 36 | 2024-2029 | |
| 53 | Iván Hernández# | 35 | 2029-2040 | |
| 53 | Jorge Lorenzo# | 35 | 2032-2042 | |
| 53 | Gustavo Peñaflor# | 35 | 2036-2042 | |
| 53 | Jon Yates | 35 | 2020-2024 | |
| 57 | Elvis Carter | 34 | 2025-2029 | |
| 57 | Steve Casey | 34 | 2021-2035 | |
| 57 | Miguel Colomo | 34 | 2039-2041 | |
| 57 | José Estrada | 34 | 2032-2039 | |
| 57 | Philip Klink | 34 | 2016-2024 | |
| 57 | José Mora# | 34 | 2031-2042 | |
| 57 | Clarence Peterson | 34 | 2017-2030 | |
| 57 | Albert Thomas | 34 | 2007-2009 | |
| 57 | Paul Watts | 34 | 2032-2034 | |
| 66 | Thurman Collins | 33 | 2019-2021 | |
| 66 | Salvador Díaz | 33 | 2007-2015 | |
| 66 | Lynn Gilbert# | 33 | 2036-2041 | |
| 66 | Randy Hall | 33 | 2007-2014 | |
| 66 | Steve Struck | 33 | 2027-2028 | |
| 66 | Haranobu Taniguchi# | 33 | 2039-2042 | |
| 66 | Joshua Waterhouse# | 33 | 2036-2040 | |
| 73 | Bill Bowden | 32 | 2014-2023 | |
| 73 | Carlos Icaza | 32 | 2018-2021 | |
| 73 | Michael Ladner | 32 | 2017-2019 | |
| 73 | Min-zhong Lou# | 32 | 2034-2035 | |
| 73 | Jorge Luna | 32 | 2024-2037 | |
| 73 | José Martínez | 32 | 2033-2041 | |
| 73 | Tsutomu Nagai# | 32 | 2039-2042 | |
| 73 | Fernando Otero | 32 | 2034-2041 | |
| 73 | Joe Parsons | 32 | 2009-2016 | |
| 73 | Ernesto Pérez# | 32 | 2037-2041 | |
| 73 | Juan Santana | 32 | 2022-2026 | |
| 73 | Barney Stone# | 32 | 2028-2038 | |
| 85 | Jorge Camarillo# | 31 | 2032-2041 | |
| 85 | José Carracheo# | 31 | 2040-2042 | |
| 85 | Kazuhiro Kanno# | 31 | 2039-2042 | |
| 85 | Jaime Melenas | 31 | 2011-2013 | |
| 85 | Damien Neighbour# | 31 | 2033-2041 | |
| 85 | Jerry Pearson | 31 | 2028-2033 | |
| 85 | Luis Serrano# | 31 | 2039-2042 | |
| 92 | Fred Arrington | 30 | 2007-2014 | |
| 92 | Pamphile Barbadori# | 30 | 2036-2042 | |
| 92 | Lloyd Caylor | 30 | 2011-2019 | |
| 92 | Adrián Cortéz | 30 | 2014-2018 | |
| 92 | Hou Hao | 30 | 2021-2033 | |
| 92 | Landon Hart | 30 | 2015-2022 | |
| 92 | Marvin Lilly | 30 | 2020-2025 | |
| 92 | Bill Martin | 30 | 2019-2032 | |
| 92 | Yajirobei Matsunaga# | 30 | 2033-2042 |
