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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | David Davis# | 46 | 2019-2030 | |
| 2 | Mike Barrett | 37 | 2022-2027 | |
| 2 | Woo-suk Cho# | 37 | 2026-2032 | |
| 4 | José Cabrera# | 35 | 2025-2028 | |
| 5 | Jesús López | 33 | 2016-2023 | |
| 5 | Bob McGhee | 33 | 2015-2028 | |
| 7 | R.J. Anderson | 31 | 2020-2027 | |
| 8 | Shawn Arnold | 30 | 2015-2022 | |
| 8 | William Bonner | 30 | 2020-2027 | |
| 8 | Louis McDowell | 30 | 2015-2030 | |
| 8 | Scott Mildren# | 30 | 2024-2027 | |
| 8 | Cisco Ortíz# | 30 | 2025-2030 | |
| 8 | Júlio Palácios | 30 | 2021-2026 | |
| 14 | Josh Gardner | 29 | 2017-2021 | |
| 14 | Salvador López# | 29 | 2029-2032 | |
| 14 | Júlio Vázquez# | 29 | 2027-2032 | |
| 17 | Paul Addison# | 28 | 2027-2031 | |
| 17 | Clay Clark | 28 | 2015-2018 | |
| 19 | Brent Riley | 27 | 2015-2025 | |
| 20 | Travis Carson# | 26 | 2020-2021 | |
| 20 | Cisco Romero | 26 | 2019-2022 | |
| 20 | Pedro Romero | 26 | 2020-2026 | |
| 20 | Rob Smith | 26 | 2018-2027 | |
| 24 | Jorge Carrión | 25 | 2022-2026 | |
| 24 | Victor de Meij# | 25 | 2025-2032 | |
| 24 | Jeff Moore | 25 | 2020-2022 | |
| 24 | Javier Roldán# | 25 | 2019-2023 | |
| 24 | Mark Tucker | 25 | 2017-2021 | |
| 29 | César González | 24 | 2021-2023 | |
| 29 | Chris Hayes# | 24 | 2023-2027 | |
| 29 | Eric Patnode | 24 | 2016-2025 | |
| 29 | Pieter Spitsbaard# | 24 | 2029-2032 | |
| 33 | Jason Ackerman | 23 | 2015-2022 | |
| 33 | Álex Carrillo | 23 | 2018-2021 | |
| 33 | António Fabián# | 23 | 2020-2028 | |
| 33 | Ralph Haggerty# | 23 | 2027-2030 | |
| 33 | Delmar Llerena# | 23 | 2026-2032 | |
| 33 | Homer O'Lannigan | 23 | 2018-2021 | |
| 33 | Hartmann Riedman# | 23 | 2024-2027 | |
| 33 | Alex Simmons | 23 | 2017-2024 | |
| 41 | Chris Burgess | 22 | 2022-2027 | |
| 41 | Atila Freska# | 22 | 2026-2028 | |
| 41 | Gerald Keller# | 22 | 2026-2029 | |
| 41 | Miguel López# | 22 | 2026-2028 | |
| 41 | Homer Shafer | 22 | 2015-2020 | |
| 41 | Ray Thibaut | 22 | 2015-2019 | |
| 41 | Orlando Uribe# | 22 | 2025-2031 | |
| 41 | José Vargo# | 22 | 2022-2024 | |
| 41 | Steven Williams | 22 | 2015-2019 | |
| 41 | Yoriyoshi Yoshimura# | 22 | 2028-2030 | |
| 51 | Elmer García# | 21 | 2021-2028 | |
| 51 | Peter Hall | 21 | 2024-2028 | |
| 51 | Andrew Holloway# | 21 | 2028-2032 | |
| 51 | Octávio Rodríguez# | 21 | 2029-2032 | |
| 51 | Mike Russell | 21 | 2018-2022 | |
| 51 | Maxwell Simon | 21 | 2024-2027 | |
| 57 | Rhett Abbott# | 20 | 2029-2031 | |
| 57 | Xavier Andrade | 20 | 2017-2022 | |
| 57 | Emory Bryant | 20 | 2015-2019 | |
| 57 | Tom Hernández | 20 | 2016-2021 | |
| 57 | Carlos Peret# | 20 | 2025-2028 | |
| 57 | Bartolo Ramírez# | 20 | 2019-2030 | |
| 57 | Wilson Vélez | 20 | 2016-2022 | |
| 64 | Mark Bell# | 19 | 2024-2031 | |
| 64 | Ken Carter | 19 | 2015-2016 | |
| 64 | Joe Lynn | 19 | 2018-2023 | |
| 64 | Richard Meyer | 19 | 2017-2021 | |
| 64 | Paul Nance | 19 | 2015-2025 | |
| 64 | José Ortíz# | 19 | 2024-2026 | |
| 70 | Sima Babic# | 18 | 2031-2032 | |
| 70 | Sid Brown | 18 | 2017-2023 | |
| 70 | Steve Bryan | 18 | 2019-2031 | |
| 70 | Freddy González | 18 | 2015-2020 | |
| 70 | Anthony Hanover | 18 | 2016-2020 | |
| 70 | Gabriel Herrera# | 18 | 2026-2032 | |
| 70 | Pedro Herrera# | 18 | 2030-2032 | |
| 70 | Greg Kelly | 18 | 2016-2020 | |
| 70 | Érico Laborde# | 18 | 2029-2030 | |
| 70 | Katsumoto Miyanohara# | 18 | 2029-2032 | |
| 70 | Vincent O'Higgin# | 18 | 2029-2031 | |
| 70 | Alonso Rodríguez | 18 | 2015-2019 | |
| 70 | Ángelo Román# | 18 | 2027-2032 | |
| 70 | Jason Troughton# | 18 | 2023-2030 | |
| 84 | Alain Arnaud# | 17 | 2029-2031 | |
| 84 | Woody Carlson# | 17 | 2018-2020 | |
| 84 | Norberto Concepción# | 17 | 2027-2028 | |
| 84 | Luis Fernández | 17 | 2015-2024 | |
| 84 | King Fletcher# | 17 | 2020-2023 | |
| 84 | Doug Green# | 17 | 2018-2020 | |
| 84 | Jesús Guerra# | 17 | 2026-2028 | |
| 84 | Teddy Jones | 17 | 2017-2019 | |
| 84 | Behar Jusufi# | 17 | 2029-2031 | |
| 84 | Oswaldo Mobray# | 17 | 2023-2024 | |
| 84 | Travis Nelson | 17 | 2024-2029 | |
| 84 | Lindsay Novak# | 17 | 2024-2031 | |
| 84 | Aurelio Ornelas# | 17 | 2026-2030 | |
| 84 | Sam Pelsize# | 17 | 2030-2032 | |
| 84 | José Rodríguez | 17 | 2015-2019 | |
| 84 | John Shirley | 17 | 2018-2025 | |
| 84 | Artie Taylor | 17 | 2017-2018 |
