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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | David Núñez | 7 | 2023-2025 | |
| 2 | Wynn Thompson | 4 | 2018-2036 | |
| 3 | Richard Davis | 3 | 2024-2026 | |
| 3 | Ken Hayes | 3 | 2024-2029 | |
| 3 | Nick Myers# | 3 | 2044-2045 | |
| 3 | Junior Ryan | 3 | 2031-2031 | |
| 3 | Jack Sandford | 3 | 2031-2034 | |
| 3 | Bill Spracklin | 3 | 2033-2036 | |
| 3 | Rory Taverner | 3 | 2021-2024 | |
| 10 | Curt Arthur# | 2 | 2047-2048 | |
| 10 | Gary Avison | 2 | 2038-2039 | |
| 10 | Carl Bean | 2 | 2043-2045 | |
| 10 | Bret Beatty# | 2 | 2047-2049 | |
| 10 | Brian Campbell | 2 | 2039-2039 | |
| 10 | Júlio Caraballo | 2 | 2029-2029 | |
| 10 | Travis Coleman# | 2 | 2047-2049 | |
| 10 | Luis Colores# | 2 | 2050-2051 | |
| 10 | Mike Conroy | 2 | 2022-2023 | |
| 10 | Nick Coomer | 2 | 2031-2034 | |
| 10 | Barrett Dobson | 2 | 2033-2034 | |
| 10 | Miguel Angel Enríquez# | 2 | 2039-2041 | |
| 10 | Miguel Fernández# | 2 | 2046-2050 | |
| 10 | Jeffrey Gómez | 2 | 2027-2039 | |
| 10 | Jorge Gonzáles# | 2 | 2045-2050 | |
| 10 | Pedro Hernández | 2 | 2048-2048 | |
| 10 | Derek Howard | 2 | 2036-2037 | |
| 10 | Jesse Johnson# | 2 | 2049-2049 | |
| 10 | Vernon Johnson | 2 | 2038-2039 | |
| 10 | Paul Lee | 2 | 2044-2045 | |
| 10 | Dan MacGruder | 2 | 2019-2020 | |
| 10 | Jean-François Massicotte | 2 | 2031-2033 | |
| 10 | Kris McCain# | 2 | 2048-2049 | |
| 10 | Bill McConnell | 2 | 2016-2016 | |
| 10 | Bert Molina | 2 | 2045-2049 | |
| 10 | David Moreno# | 2 | 2049-2051 | |
| 10 | Seinosuke Murakami | 2 | 2020-2023 | |
| 10 | Barry Norwood | 2 | 2036-2037 | |
| 10 | Terry Ramsey | 2 | 2014-2019 | |
| 10 | Javier Reyna# | 2 | 2050-2051 | |
| 10 | Jack Robinson | 2 | 2029-2031 | |
| 10 | Chris Shield# | 2 | 2042-2051 | |
| 10 | Chris Spencer | 2 | 2013-2017 | |
| 10 | Toby Valentín# | 2 | 2049-2050 | |
| 10 | Henry Valentine | 2 | 2018-2020 | |
| 10 | Lonnie Wilson | 2 | 2016-2020 | |
| 10 | Eugene Woods | 2 | 2031-2033 | |
| 47 | Erik Alexander# | 1 | 2047-2050 | |
| 47 | Lúcio Alonso# | 1 | 2045-2046 | |
| 47 | Howard Anderson# | 1 | 2042-2042 | |
| 47 | Francisco Andrés# | 1 | 2046-2047 | |
| 47 | Guillermo Ayala | 1 | 2025-2025 | |
| 47 | Eric Bane# | 1 | 2050-2051 | |
| 47 | Ramón Bañuelos# | 1 | 2048-2048 | |
| 47 | Edward Barnes# | 1 | 2046-2047 | |
| 47 | Jared Bergeron# | 1 | 2049-2050 | |
| 47 | Lowell Blankenbecker# | 1 | 2048-2051 | |
| 47 | David Bridges | 1 | 2020-2021 | |
| 47 | Reese Browning# | 1 | 2045-2049 | |
| 47 | Leon Calhoun# | 1 | 2042-2051 | |
| 47 | Duane Carter | 1 | 2019-2026 | |
| 47 | Peter Carter | 1 | 2020-2026 | |
| 47 | Lorenzo Castaneda | 1 | 2038-2039 | |
| 47 | Peyton Chambers# | 1 | 2046-2047 | |
| 47 | Miguel Chávez | 1 | 2030-2032 | |
| 47 | Rubén Chávez# | 1 | 2048-2048 | |
| 47 | William Cokinbred | 1 | 2023-2024 | |
| 47 | Mike Cook | 1 | 2032-2033 | |
| 47 | Rafael Cota | 1 | 2021-2022 | |
| 47 | Pat Curtis | 1 | 2030-2031 | |
| 47 | Steve Davis# | 1 | 2045-2051 | |
| 47 | Bernardo De Jesús# | 1 | 2044-2045 | |
| 47 | José Díaz | 1 | 2024-2024 | |
| 47 | Luis Díaz | 1 | 2031-2032 | |
| 47 | Ed Dixon | 1 | 2015-2016 | |
| 47 | Rick Dooley | 1 | 2026-2032 | |
| 47 | Rod Duncan | 1 | 2041-2042 | |
| 47 | Fernão Ega# | 1 | 2049-2051 | |
| 47 | Javier Escobar | 1 | 2019-2020 | |
| 47 | Roberto Escobar# | 1 | 2048-2049 | |
| 47 | Jacob Fields# | 1 | 2044-2046 | |
| 47 | Edmund Fitzgerald | 1 | 2021-2022 | |
| 47 | Dale Fleming# | 1 | 2045-2045 | |
| 47 | Max Frankcombe# | 1 | 2047-2051 | |
| 47 | Eduardo García# | 1 | 2049-2050 | |
| 47 | Javier García | 1 | 2026-2026 | |
| 47 | Ben George | 1 | 2031-2031 | |
| 47 | Gene Gibson | 1 | 2014-2014 | |
| 47 | Ramiro Gonzáles# | 1 | 2048-2049 | |
| 47 | Felipe González# | 1 | 2047-2048 | |
| 47 | Dover Graves | 1 | 2013-2013 | |
| 47 | John Hall | 1 | 2029-2031 | |
| 47 | Kelly Hanes# | 1 | 2046-2046 | |
| 47 | Eduardo Hernández | 1 | 2035-2036 | |
| 47 | Francisco Hernández# | 1 | 2043-2044 | |
| 47 | Jonathan Hernández | 1 | 2030-2031 | |
| 47 | Juan Hernández# | 1 | 2048-2049 | |
| 47 | Toshikazu Higashi | 1 | 2019-2020 | |
| 47 | Larry Hill# | 1 | 2048-2051 | |
| 47 | Willis Hines | 1 | 2027-2038 | |
| 47 | Dan Hinton | 1 | 2017-2017 |
