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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Raúl Pérez | 51 | 2015-2028 | |
| 2 | Fernando Reyna | 46 | 2015-2027 | |
| 3 | Miguel Mora | 43 | 2015-2020 | |
| 4 | José Santiago# | 41 | 2028-2032 | |
| 5 | Romano Martínez# | 36 | 2024-2029 | |
| 5 | Horace McKenzie# | 36 | 2016-2021 | |
| 7 | Zane Reed | 35 | 2017-2028 | |
| 8 | Il-gyung Kim | 34 | 2017-2026 | |
| 8 | Tomiji Saikawa | 34 | 2023-2028 | |
| 10 | Currito Melena# | 31 | 2025-2030 | |
| 10 | Javier Penela | 31 | 2015-2020 | |
| 12 | Miguel González | 30 | 2015-2018 | |
| 12 | Esteban Miroz# | 30 | 2027-2032 | |
| 14 | Luis Castrejón# | 29 | 2019-2031 | |
| 14 | Xavier Padilla# | 29 | 2025-2031 | |
| 16 | Carlos Díaz# | 28 | 2022-2028 | |
| 17 | Víctor García# | 27 | 2017-2021 | |
| 17 | Juan Núñez | 27 | 2015-2018 | |
| 19 | Jeff Moore | 26 | 2015-2017 | |
| 19 | Bob Payne# | 26 | 2025-2027 | |
| 19 | Plinio Pedrulho# | 26 | 2020-2030 | |
| 19 | Haden Pittman# | 26 | 2023-2026 | |
| 19 | Jorge Velázquez | 26 | 2017-2025 | |
| 24 | Jeremy Petty | 25 | 2018-2023 | |
| 24 | Steve Tedder# | 25 | 2030-2032 | |
| 24 | Félix Torres | 25 | 2021-2026 | |
| 27 | Lawrence Bignold | 24 | 2016-2018 | |
| 27 | John Buck | 24 | 2015-2018 | |
| 27 | Ricardo Fraga# | 24 | 2030-2032 | |
| 27 | Júlio Hernández | 24 | 2015-2019 | |
| 27 | Xavier Navarro | 24 | 2023-2026 | |
| 27 | James Scott | 24 | 2018-2029 | |
| 27 | Ipe Talboom | 24 | 2024-2028 | |
| 34 | Tony Alfonso# | 23 | 2029-2030 | |
| 34 | Ryan Bentley# | 23 | 2022-2024 | |
| 34 | Ryan Ingram | 23 | 2023-2027 | |
| 34 | Gustavo Pérez# | 23 | 2018-2024 | |
| 38 | Alfonso Álvarez# | 22 | 2018-2022 | |
| 38 | John Fowler | 22 | 2017-2019 | |
| 38 | Sam MacKerras | 22 | 2017-2022 | |
| 38 | Pat Pérez | 22 | 2020-2022 | |
| 38 | John Tanner | 22 | 2015-2019 | |
| 43 | Larry Branch | 21 | 2015-2023 | |
| 43 | Jorge Cruz# | 21 | 2025-2032 | |
| 43 | Elroy Gardner | 21 | 2015-2019 | |
| 43 | Ricky Jackson | 21 | 2019-2024 | |
| 43 | Victor Lustig# | 21 | 2029-2032 | |
| 43 | Morgan MacDonald | 21 | 2017-2022 | |
| 43 | Kyle MacRae# | 21 | 2025-2031 | |
| 43 | Leif Mayer | 21 | 2026-2028 | |
| 43 | Fernando Peralta | 21 | 2017-2019 | |
| 52 | António Aguilar | 20 | 2015-2018 | |
| 52 | Pat Brown | 20 | 2018-2020 | |
| 52 | Tony Cherena | 20 | 2015-2016 | |
| 52 | Fernando Durán | 20 | 2023-2026 | |
| 52 | Neil Gilliam | 20 | 2015-2030 | |
| 52 | Damien Hayward# | 20 | 2028-2029 | |
| 52 | Rizaldo Manansala# | 20 | 2029-2032 | |
| 52 | Harry Mander# | 20 | 2024-2030 | |
| 52 | José Martínez | 20 | 2020-2023 | |
| 52 | Bryan McKinney# | 20 | 2026-2027 | |
| 52 | Don Miller# | 20 | 2018-2019 | |
| 52 | Satoshi Ono# | 20 | 2030-2032 | |
| 64 | Austin Abbott | 19 | 2015-2018 | |
| 64 | Jeremy de Vos | 19 | 2022-2025 | |
| 64 | Hank Downey | 19 | 2017-2025 | |
| 64 | Cameron Frye# | 19 | 2024-2025 | |
| 64 | Jules Goux# | 19 | 2027-2031 | |
| 64 | Ernest Gunter | 19 | 2015-2024 | |
| 64 | Jason Hamilton# | 19 | 2020-2022 | |
| 64 | Matt Harris | 19 | 2015-2019 | |
| 64 | Ash Ibarra# | 19 | 2025-2027 | |
| 64 | Javier López | 19 | 2016-2018 | |
| 64 | Kenny Ryan | 19 | 2020-2024 | |
| 64 | Masahiro Sakei# | 19 | 2030-2031 | |
| 64 | Poto Scacceri# | 19 | 2029-2031 | |
| 64 | Pedro Silva# | 19 | 2024-2028 | |
| 64 | Alberto Solís# | 19 | 2029-2032 | |
| 64 | Joaquín Soto | 19 | 2016-2019 | |
| 64 | Tomás Torres | 19 | 2020-2023 | |
| 81 | Alejandro Arteaga# | 18 | 2019-2021 | |
| 81 | Eduardo Bravo | 18 | 2017-2024 | |
| 81 | Luis Domínguez# | 18 | 2026-2032 | |
| 81 | Kyung-nam Kim# | 18 | 2030-2032 | |
| 81 | Jack King | 18 | 2017-2019 | |
| 81 | Mario López# | 18 | 2029-2032 | |
| 81 | Mauro Marín | 18 | 2015-2024 | |
| 81 | Juan Martínez | 18 | 2019-2030 | |
| 81 | Emershan Naidoo# | 18 | 2026-2027 | |
| 81 | Roberto Silva# | 18 | 2025-2026 | |
| 81 | Nobuhito Tanaka# | 18 | 2029-2031 | |
| 81 | Bill Washington | 18 | 2017-2019 | |
| 93 | Domingo Álvarez# | 17 | 2018-2020 | |
| 93 | Terry Dwyer | 17 | 2015-2022 | |
| 93 | R.J. Good | 17 | 2016-2019 | |
| 93 | Tim Harris | 17 | 2015-2022 | |
| 93 | Tom Jones | 17 | 2016-2022 | |
| 93 | Ismael Lara# | 17 | 2028-2032 | |
| 93 | Javier Luna# | 17 | 2025-2031 | |
| 93 | Juan Méndez | 17 | 2022-2023 |
