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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | José Ayala# | 31 | 2019-2024 | |
| 1 | Ulises Perez# | 31 | 2015-2019 | |
| 3 | William Heflin# | 28 | 2019-2023 | |
| 4 | Jesús Cuevas# | 27 | 2025-2027 | |
| 5 | Juan Hernández# | 26 | 2021-2027 | |
| 5 | Jose Paulino# | 26 | 2012-2021 | |
| 5 | Juan Rodríguez# | 26 | 2020-2024 | |
| 8 | Reynaldo Polanco# | 25 | 2010-2017 | |
| 9 | José Castillo# | 24 | 2022-2026 | |
| 9 | Don Dodson# | 24 | 2025-2027 | |
| 9 | Orlando Ortíz# | 24 | 2021-2023 | |
| 9 | António Vázquez# | 24 | 2025-2028 | |
| 13 | Alfredo Martínez# | 21 | 2025-2026 | |
| 13 | António Rodríguez# | 21 | 2023-2026 | |
| 13 | Everton Tickle# | 21 | 2022-2026 | |
| 16 | Tony Cruz# | 20 | 2021-2025 | |
| 16 | Victor Done# | 20 | 2013-2018 | |
| 16 | Pancho Gallegos# | 20 | 2024-2027 | |
| 16 | Luis Ramos# | 20 | 2012-2017 | |
| 20 | Nelson Durán# | 19 | 2021-2023 | |
| 20 | Juan Gabriel# | 19 | 2021-2024 | |
| 20 | Juan García# | 19 | 2025-2027 | |
| 20 | Resly Linares# | 19 | 2015-2019 | |
| 24 | Razvan Corodeanu# | 18 | 2021-2025 | |
| 24 | Norberto Espinoza# | 18 | 2021-2023 | |
| 24 | Jose Ma. Gonzalez# | 18 | 2016-2019 | |
| 24 | Jeifrey Nunez# | 18 | 2015-2020 | |
| 24 | Jesús Santos# | 18 | 2024-2026 | |
| 24 | Michael Teague# | 18 | 2025-2028 | |
| 24 | Tomás Villarreal# | 18 | 2025-2028 | |
| 31 | Jorge Calderón# | 17 | 2021-2024 | |
| 31 | Jonathan Davies# | 17 | 2025-2027 | |
| 31 | Graham Limb# | 17 | 2024-2026 | |
| 31 | Cesar Medina# | 17 | 2012-2016 | |
| 31 | Merkis Montero# | 17 | 2013-2018 | |
| 31 | Dan Phillips# | 17 | 2022-2023 | |
| 31 | Ellis Raymont# | 17 | 2022-2025 | |
| 31 | Andy Robles# | 17 | 2021-2023 | |
| 31 | Jorge Rodríguez# | 17 | 2025-2027 | |
| 31 | Julián Sánchez# | 17 | 2021-2024 | |
| 41 | José Berroa# | 16 | 2024-2027 | |
| 41 | Randy Brewster# | 16 | 2022-2024 | |
| 41 | Jo-hsi Chien# | 16 | 2025-2027 | |
| 41 | Juan Gómez# | 16 | 2025-2028 | |
| 41 | Ánibal González# | 16 | 2019-2020 | |
| 41 | Brody Herbert# | 16 | 2026-2027 | |
| 41 | José Hernández# | 16 | 2023-2027 | |
| 41 | Jeremy Leach# | 16 | 2020-2024 | |
| 41 | Jaimito Lebron# | 16 | 2014-2018 | |
| 41 | Sandy Lugo# | 16 | 2014-2021 | |
| 41 | José Negre# | 16 | 2025-2027 | |
| 41 | Jeff Niemann | 16 | 2015-2015 | |
| 41 | Ken Ruttman# | 16 | 2021-2024 | |
| 54 | Xadreque Blanco# | 15 | 2023-2025 | |
| 54 | Mutsuhito Chikafuji# | 15 | 2025-2026 | |
| 54 | Luis Cortéz# | 15 | 2022-2026 | |
| 54 | Héctor Estrada# | 15 | 2024-2027 | |
| 54 | Francis Ganderton# | 15 | 2023-2026 | |
| 54 | Luis García# | 15 | 2021-2024 | |
| 54 | José Garza# | 15 | 2025-2028 | |
| 54 | Jeff Hill# | 15 | 2025-2027 | |
| 54 | Dauri Moreta | 15 | 2016-2019 | |
| 54 | Tomás Palmeiro# | 15 | 2022-2026 | |
| 54 | Luis Al. Pena | 15 | 2015-2020 | |
| 54 | Romăo Quintela# | 15 | 2024-2026 | |
| 54 | José Valéncia# | 15 | 2018-2020 | |
| 54 | Toby Woodings# | 15 | 2023-2027 | |
| 68 | Don Anderson# | 14 | 2025-2028 | |
| 68 | Jeff Bradburn# | 14 | 2021-2024 | |
| 68 | José Fernández# | 14 | 2025-2027 | |
| 68 | José Hernández# | 14 | 2026-2027 | |
| 68 | Jorge Lete# | 14 | 2020-2024 | |
| 68 | Jesús Luér# | 14 | 2022-2023 | |
| 68 | Juan Luna# | 14 | 2021-2024 | |
| 68 | Tony Ortíz# | 14 | 2024-2027 | |
| 68 | Domingo Pena# | 14 | 2015-2020 | |
| 68 | Richelson Pena | 14 | 2011-2013 | |
| 68 | Freddy Rodríguez# | 14 | 2020-2021 | |
| 68 | Javier Rodriguez# | 14 | 2012-2017 | |
| 68 | Jhon Meison Taylor# | 14 | 2025-2026 | |
| 68 | Esteban Velásquez# | 14 | 2025-2027 | |
| 68 | Heriberto Ventura# | 14 | 2017-2020 | |
| 83 | Enrico Barbosa# | 13 | 2022-2026 | |
| 83 | T.J. Bethencourt# | 13 | 2025-2027 | |
| 83 | Juan Carriles# | 13 | 2024-2027 | |
| 83 | Bertrand Elvidge# | 13 | 2025-2028 | |
| 83 | Ángelo Gil# | 13 | 2018-2020 | |
| 83 | Gilberto Hernández# | 13 | 2021-2026 | |
| 83 | Juan Longoria# | 13 | 2026-2028 | |
| 83 | Ernesto López# | 13 | 2025-2027 | |
| 83 | Sean MacCurtin# | 13 | 2025-2028 | |
| 83 | Ángelo Martínez# | 13 | 2023-2027 | |
| 83 | Sam McCray# | 13 | 2022-2026 | |
| 83 | José Antonio Mejía# | 13 | 2022-2026 | |
| 83 | Min-tae Na# | 13 | 2022-2024 | |
| 83 | Jorge Nava# | 13 | 2025-2027 | |
| 83 | Mayky Perez | 13 | 2014-2017 | |
| 83 | José Ramales# | 13 | 2026-2028 | |
| 83 | Denyi Reyes | 13 | 2016-2020 | |
| 83 | José Rodríguez# | 13 | 2015-2018 |
