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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 | Esteban Miroz# | 31 | 2027-2033 | |
| 10 | Javier Penela | 31 | 2015-2020 | |
| 10 | Steve Tedder# | 31 | 2030-2033 | |
| 14 | Miguel González | 30 | 2015-2018 | |
| 15 | Luis Castrejón# | 29 | 2019-2031 | |
| 15 | Ricardo Fraga# | 29 | 2030-2033 | |
| 15 | Xavier Padilla# | 29 | 2025-2031 | |
| 18 | Carlos Díaz# | 28 | 2022-2028 | |
| 19 | Víctor García# | 27 | 2017-2021 | |
| 19 | Juan Núñez | 27 | 2015-2018 | |
| 21 | Jeff Moore | 26 | 2015-2017 | |
| 21 | Satoshi Ono# | 26 | 2030-2033 | |
| 21 | Bob Payne# | 26 | 2025-2027 | |
| 21 | Plinio Pedrulho# | 26 | 2020-2030 | |
| 21 | Haden Pittman | 26 | 2023-2026 | |
| 21 | Jorge Velázquez | 26 | 2017-2025 | |
| 27 | Jeremy Petty | 25 | 2018-2023 | |
| 27 | Félix Torres | 25 | 2021-2026 | |
| 29 | Lawrence Bignold | 24 | 2016-2018 | |
| 29 | John Buck | 24 | 2015-2018 | |
| 29 | Júlio Hernández | 24 | 2015-2019 | |
| 29 | Kyung-nam Kim# | 24 | 2030-2033 | |
| 29 | Victor Lustig# | 24 | 2029-2033 | |
| 29 | Xavier Navarro | 24 | 2023-2026 | |
| 29 | James Scott | 24 | 2018-2029 | |
| 29 | Ipe Talboom | 24 | 2024-2028 | |
| 37 | Tony Alfonso# | 23 | 2029-2030 | |
| 37 | Ryan Bentley# | 23 | 2022-2024 | |
| 37 | Ryan Ingram | 23 | 2023-2027 | |
| 37 | Gustavo Pérez# | 23 | 2018-2024 | |
| 41 | Alfonso Álvarez# | 22 | 2018-2022 | |
| 41 | Zion DeBose# | 22 | 2030-2033 | |
| 41 | John Fowler | 22 | 2017-2019 | |
| 41 | Sam MacKerras | 22 | 2017-2022 | |
| 41 | Pat Pérez | 22 | 2020-2022 | |
| 41 | John Tanner | 22 | 2015-2019 | |
| 47 | Larry Branch | 21 | 2015-2023 | |
| 47 | Jorge Cruz# | 21 | 2025-2032 | |
| 47 | Luis Domínguez# | 21 | 2026-2033 | |
| 47 | Elroy Gardner | 21 | 2015-2019 | |
| 47 | Ricky Jackson | 21 | 2019-2024 | |
| 47 | Morgan MacDonald | 21 | 2017-2022 | |
| 47 | Kyle MacRae# | 21 | 2025-2031 | |
| 47 | Leif Mayer | 21 | 2026-2028 | |
| 47 | Fernando Peralta | 21 | 2017-2019 | |
| 56 | António Aguilar | 20 | 2015-2018 | |
| 56 | Pat Brown | 20 | 2018-2020 | |
| 56 | Tony Cherena | 20 | 2015-2016 | |
| 56 | Fernando Durán | 20 | 2023-2026 | |
| 56 | Neil Gilliam | 20 | 2015-2030 | |
| 56 | Damien Hayward# | 20 | 2028-2029 | |
| 56 | Ismael Lara# | 20 | 2028-2033 | |
| 56 | Rizaldo Manansala# | 20 | 2029-2032 | |
| 56 | Harry Mander# | 20 | 2024-2030 | |
| 56 | José Martínez | 20 | 2020-2023 | |
| 56 | Bryan McKinney# | 20 | 2026-2027 | |
| 56 | Don Miller# | 20 | 2018-2019 | |
| 56 | Andrew Prieto# | 20 | 2031-2033 | |
| 69 | Austin Abbott | 19 | 2015-2018 | |
| 69 | Jeremy de Vos | 19 | 2022-2025 | |
| 69 | Hank Downey | 19 | 2017-2025 | |
| 69 | Cameron Frye# | 19 | 2024-2025 | |
| 69 | Jules Goux# | 19 | 2027-2033 | |
| 69 | Ernest Gunter | 19 | 2015-2024 | |
| 69 | Jason Hamilton# | 19 | 2020-2022 | |
| 69 | Matt Harris | 19 | 2015-2019 | |
| 69 | Ash Ibarra# | 19 | 2025-2027 | |
| 69 | Javier López | 19 | 2016-2018 | |
| 69 | Kenny Ryan | 19 | 2020-2024 | |
| 69 | Masahiro Sakei# | 19 | 2030-2031 | |
| 69 | Poto Scacceri# | 19 | 2029-2031 | |
| 69 | Pedro Silva# | 19 | 2024-2028 | |
| 69 | Alberto Solís# | 19 | 2029-2032 | |
| 69 | Joaquín Soto | 19 | 2016-2019 | |
| 69 | Tomás Torres | 19 | 2020-2023 | |
| 86 | Alejandro Arteaga# | 18 | 2019-2021 | |
| 86 | Eduardo Bravo | 18 | 2017-2024 | |
| 86 | Jack King | 18 | 2017-2019 | |
| 86 | Mario López# | 18 | 2029-2033 | |
| 86 | Mauro Marín | 18 | 2015-2024 | |
| 86 | Juan Martínez | 18 | 2019-2030 | |
| 86 | Emershan Naidoo# | 18 | 2026-2027 | |
| 86 | Roberto Silva# | 18 | 2025-2026 | |
| 86 | Nobuhito Tanaka# | 18 | 2029-2031 | |
| 86 | Dylan Telford# | 18 | 2032-2033 | |
| 86 | Bill Washington | 18 | 2017-2019 | |
| 97 | Domingo Álvarez# | 17 | 2018-2020 | |
| 97 | Terry Dwyer | 17 | 2015-2022 | |
| 97 | Alejandro García# | 17 | 2032-2033 | |
| 97 | R.J. Good | 17 | 2016-2019 |
