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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Bernardo Romero | 57 | 2019-2025 | |
| 2 | Alberto García# | 48 | 2029-2032 | |
| 3 | Tsugahara Suzuki | 47 | 2021-2024 | |
| 4 | Manuel Ramírez# | 43 | 2032-2036 | |
| 5 | Xavier Bergeron | 41 | 2018-2022 | |
| 6 | Nelson Béltre# | 40 | 2021-2026 | |
| 6 | Mike Stabler | 40 | 2015-2020 | |
| 8 | Danny Owen# | 39 | 2030-2034 | |
| 9 | William Bryan | 38 | 2021-2025 | |
| 9 | Thierry Garneau | 38 | 2013-2016 | |
| 9 | Toshikasu Kiyomizu | 38 | 2017-2020 | |
| 12 | José Morales# | 35 | 2032-2036 | |
| 12 | Jon Vaughn# | 35 | 2024-2027 | |
| 14 | Mike Thomas# | 34 | 2036-2038 | |
| 15 | Edgardo González | 33 | 2008-2010 | |
| 15 | Juan González | 33 | 2013-2015 | |
| 17 | Carlos Castillo | 32 | 2020-2024 | |
| 17 | Roy March | 32 | 2017-2021 | |
| 19 | Calvin Jones# | 31 | 2035-2038 | |
| 19 | Mario Tobías | 31 | 2013-2014 | |
| 21 | Tomás Molina | 30 | 2020-2022 | |
| 21 | Tomiji Takuda | 30 | 2013-2016 | |
| 23 | Jesús De Los Santos# | 29 | 2024-2026 | |
| 23 | Gabriel García# | 29 | 2030-2032 | |
| 23 | Don Sutherland | 29 | 2020-2025 | |
| 26 | Daron Chandler# | 28 | 2033-2035 | |
| 26 | Chris Fields# | 28 | 2034-2037 | |
| 26 | Jung-ha Kim | 28 | 2010-2013 | |
| 26 | Naonobu Takahashi# | 28 | 2030-2034 | |
| 30 | Júlio Aguilar | 27 | 2021-2025 | |
| 30 | Anthony Bowen# | 27 | 2036-2038 | |
| 30 | Ángel Estrada# | 27 | 2027-2030 | |
| 30 | Ramón Fonseca | 27 | 2018-2021 | |
| 30 | Ray Gordon# | 27 | 2029-2032 | |
| 30 | Roberto Moreno | 27 | 2022-2024 | |
| 30 | Javier Pérez# | 27 | 2033-2035 | |
| 30 | Júlio Pérez# | 27 | 2030-2032 | |
| 30 | Eric Robertson# | 27 | 2033-2037 | |
| 30 | William Tagg | 27 | 2013-2015 | |
| 40 | Reynaldo García | 26 | 2011-2016 | |
| 40 | Terry Hoffman# | 26 | 2030-2033 | |
| 40 | Ernesto Mendoza# | 26 | 2024-2027 | |
| 40 | Nick Parks | 26 | 2022-2024 | |
| 44 | José Fernández# | 25 | 2027-2028 | |
| 44 | Will Ferreira# | 25 | 2034-2035 | |
| 44 | Juan Gómez# | 25 | 2030-2033 | |
| 44 | Luis Gonzáles# | 25 | 2033-2035 | |
| 44 | Jesús González | 25 | 2024-2026 | |
| 44 | Dae-ho Kim# | 25 | 2022-2025 | |
| 44 | Sloan Otto | 25 | 2013-2016 | |
| 44 | Beau Richards | 25 | 2013-2014 | |
| 44 | Jing Woo# | 25 | 2031-2034 | |
| 53 | Henry Brown | 24 | 2024-2027 | |
| 53 | Neil Jensen# | 24 | 2035-2037 | |
| 53 | Bill McLean# | 24 | 2031-2032 | |
| 53 | Luis Ramírez | 24 | 2024-2026 | |
| 53 | Héctor Ramos# | 24 | 2034-2037 | |
| 53 | Luis Rosado# | 24 | 2029-2032 | |
| 53 | José Sánchez | 24 | 2013-2020 | |
| 53 | Carlos Sandoval# | 24 | 2035-2038 | |
| 53 | John Snow | 24 | 2007-2009 | |
| 53 | Zi-jing Yong# | 24 | 2032-2035 | |
| 53 | Hyun-soo Yun | 24 | 2010-2010 | |
| 64 | Roberto Carrillo# | 23 | 2025-2027 | |
| 64 | Sergio Chávez# | 23 | 2024-2028 | |
| 64 | Ángel Gil# | 23 | 2028-2030 | |
| 64 | Bret Hendricks# | 23 | 2029-2031 | |
| 64 | Kenshin Kubota | 23 | 2020-2024 | |
| 64 | John Lane | 23 | 2016-2019 | |
| 64 | Albert Lebel* | 23 | 2013-2015 | |
| 64 | Rob Lucas | 23 | 2021-2025 | |
| 64 | Owen Martínez# | 23 | 2036-2038 | |
| 64 | Honorato Mota | 23 | 2019-2021 | |
| 64 | César Rodríguez | 23 | 2022-2029 | |
| 64 | Mark Schlosser# | 23 | 2030-2032 | |
| 76 | Alberto Colón | 22 | 2028-2031 | |
| 76 | Manuel González# | 22 | 2025-2027 | |
| 76 | Rafael López# | 22 | 2024-2026 | |
| 76 | Juan Ochoa | 22 | 2029-2031 | |
| 76 | Armando Quiñones# | 22 | 2036-2038 | |
| 76 | Júlio Torres | 22 | 2021-2024 | |
| 82 | Mark Austin# | 21 | 2037-2038 | |
| 82 | Bob Coture | 21 | 2007-2009 | |
| 82 | Lonnie Dodson# | 21 | 2031-2033 | |
| 82 | José Gabriel# | 21 | 2029-2032 | |
| 82 | Miguel Galván# | 21 | 2025-2026 | |
| 82 | Sixto García | 21 | 2025-2029 | |
| 82 | Vaughan Gillespie | 21 | 2020-2024 | |
| 82 | Sean Hart | 21 | 2027-2030 | |
| 82 | Dave Martin | 21 | 2027-2030 | |
| 82 | Carlos Ortíz# | 21 | 2025-2030 | |
| 82 | Jaap Oskam# | 21 | 2032-2035 | |
| 82 | Isaac Pope | 21 | 2024-2027 | |
| 82 | Ignacio Ríos | 21 | 2011-2013 | |
| 82 | Vicente Ríos# | 21 | 2035-2038 | |
| 82 | Lorenzo Sánchez | 21 | 2021-2023 | |
| 82 | Héctor Vásquez | 21 | 2008-2009 | |
| 98 | Gianni Bertetto# | 20 | 2032-2034 | |
| 98 | Bryce Borrell# | 20 | 2031-2035 | |
| 98 | José Delgado# | 20 | 2035-2038 |
