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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 | Horace McKenzie# | 36 | 2016-2021 | |
| 5 | Zane Reed# | 35 | 2017-2028 | |
| 6 | Il-gyung Kim | 34 | 2017-2026 | |
| 6 | Romano Martínez# | 34 | 2024-2028 | |
| 6 | Tomiji Saikawa# | 34 | 2023-2028 | |
| 9 | Javier Penela | 31 | 2015-2020 | |
| 10 | Miguel González | 30 | 2015-2018 | |
| 11 | Carlos Díaz# | 28 | 2022-2028 | |
| 12 | Víctor García# | 27 | 2017-2021 | |
| 12 | Juan Núñez | 27 | 2015-2018 | |
| 14 | Jeff Moore | 26 | 2015-2017 | |
| 14 | Bob Payne# | 26 | 2025-2027 | |
| 14 | Haden Pittman# | 26 | 2023-2026 | |
| 14 | Jorge Velázquez | 26 | 2017-2025 | |
| 18 | Jeremy Petty | 25 | 2018-2023 | |
| 18 | Félix Torres | 25 | 2021-2026 | |
| 20 | Lawrence Bignold# | 24 | 2016-2018 | |
| 20 | John Buck | 24 | 2015-2018 | |
| 20 | Júlio Hernández | 24 | 2015-2019 | |
| 20 | Xavier Navarro# | 24 | 2023-2026 | |
| 20 | Ipe Talboom# | 24 | 2024-2028 | |
| 25 | Ryan Bentley# | 23 | 2022-2024 | |
| 25 | Ryan Ingram | 23 | 2023-2027 | |
| 25 | Gustavo Pérez# | 23 | 2018-2024 | |
| 28 | Alfonso Álvarez# | 22 | 2018-2022 | |
| 28 | John Fowler | 22 | 2017-2019 | |
| 28 | Sam MacKerras | 22 | 2017-2022 | |
| 28 | Xavier Padilla# | 22 | 2025-2028 | |
| 28 | Pat Pérez# | 22 | 2020-2022 | |
| 28 | James Scott# | 22 | 2018-2021 | |
| 28 | John Tanner | 22 | 2015-2019 | |
| 35 | Larry Branch | 21 | 2015-2023 | |
| 35 | Elroy Gardner | 21 | 2015-2019 | |
| 35 | Ricky Jackson# | 21 | 2019-2024 | |
| 35 | Morgan MacDonald | 21 | 2017-2022 | |
| 35 | Leif Mayer# | 21 | 2026-2028 | |
| 35 | Fernando Peralta# | 21 | 2017-2019 | |
| 41 | António Aguilar | 20 | 2015-2018 | |
| 41 | Pat Brown | 20 | 2018-2020 | |
| 41 | Tony Cherena | 20 | 2015-2016 | |
| 41 | Fernando Durán# | 20 | 2023-2026 | |
| 41 | Neil Gilliam# | 20 | 2015-2018 | |
| 41 | José Martínez# | 20 | 2020-2023 | |
| 41 | Bryan McKinney# | 20 | 2026-2027 | |
| 41 | Don Miller# | 20 | 2018-2019 | |
| 49 | Austin Abbott | 19 | 2015-2018 | |
| 49 | Luis Castrejón# | 19 | 2019-2026 | |
| 49 | Jeremy de Vos# | 19 | 2022-2025 | |
| 49 | Hank Downey# | 19 | 2017-2025 | |
| 49 | Cameron Frye# | 19 | 2024-2025 | |
| 49 | Ernest Gunter | 19 | 2015-2024 | |
| 49 | Jason Hamilton# | 19 | 2020-2022 | |
| 49 | Matt Harris# | 19 | 2015-2019 | |
| 49 | Ash Ibarra# | 19 | 2025-2027 | |
| 49 | Javier López# | 19 | 2016-2018 | |
| 49 | Kenny Ryan | 19 | 2020-2024 | |
| 49 | Pedro Silva# | 19 | 2024-2028 | |
| 49 | Joaquín Soto | 19 | 2016-2019 | |
| 49 | Tomás Torres# | 19 | 2020-2023 | |
| 63 | Alejandro Arteaga# | 18 | 2019-2021 | |
| 63 | Eduardo Bravo# | 18 | 2017-2024 | |
| 63 | Jack King# | 18 | 2017-2019 | |
| 63 | Mauro Marín | 18 | 2015-2024 | |
| 63 | Emershan Naidoo# | 18 | 2026-2027 | |
| 63 | Plinio Pedrulho# | 18 | 2020-2022 | |
| 63 | Roberto Silva# | 18 | 2025-2026 | |
| 63 | Bill Washington | 18 | 2017-2019 | |
| 71 | Domingo Álvarez# | 17 | 2018-2020 | |
| 71 | Terry Dwyer | 17 | 2015-2022 | |
| 71 | R.J. Good | 17 | 2016-2019 | |
| 71 | Tim Harris | 17 | 2015-2022 | |
| 71 | Tom Jones | 17 | 2016-2022 | |
| 71 | Juan Méndez# | 17 | 2022-2023 | |
| 71 | Ed O'Quinn# | 17 | 2026-2027 | |
| 78 | Jeff Burrell# | 16 | 2015-2018 | |
| 78 | Doug Freeth# | 16 | 2026-2028 | |
| 78 | Gus Gamble# | 16 | 2024-2028 | |
| 78 | Rob Hanson | 16 | 2016-2022 | |
| 78 | Bobby Irvine# | 16 | 2026-2028 | |
| 78 | Juan Martínez# | 16 | 2019-2023 | |
| 78 | Denis Melis# | 16 | 2023-2028 | |
| 78 | Alberto Seguillo | 16 | 2015-2018 | |
| 78 | Ken Shelton# | 16 | 2019-2027 | |
| 78 | Hallinan Udny | 16 | 2015-2018 | |
| 78 | Frank Veeck# | 16 | 2026-2027 | |
| 78 | Stewart Walker | 16 | 2016-2020 | |
| 78 | Stanley Yelnats# | 16 | 2026-2027 | |
| 91 | Richard Allison# | 15 | 2015-2016 | |
| 91 | Calvin Beck# | 15 | 2023-2025 | |
| 91 | Robert Bell | 15 | 2020-2022 | |
| 91 | James Dockery# | 15 | 2026-2027 | |
| 91 | Severiano Duclos# | 15 | 2020-2022 | |
| 91 | Wallace Elgie# | 15 | 2016-2025 | |
| 91 | Octávio Fernández# | 15 | 2024-2026 | |
| 91 | Zalontae Hillary# | 15 | 2027-2028 | |
| 91 | Pat Hunt# | 15 | 2020-2028 | |
| 91 | Yoshida Kudo# | 15 | 2023-2028 |
