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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 | |
| 3 | Woo-suk Cho# | 36 | 2026-2030 | |
| 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 | |
| 15 | Clay Clark | 28 | 2015-2018 | |
| 16 | Paul Addison# | 27 | 2027-2030 | |
| 16 | Brent Riley | 27 | 2015-2025 | |
| 18 | Travis Carson# | 26 | 2020-2021 | |
| 18 | Cisco Romero | 26 | 2019-2022 | |
| 18 | Pedro Romero | 26 | 2020-2026 | |
| 18 | Rob Smith# | 26 | 2018-2027 | |
| 22 | Jorge Carrión# | 25 | 2022-2026 | |
| 22 | Jeff Moore | 25 | 2020-2022 | |
| 22 | Javier Roldán# | 25 | 2019-2023 | |
| 22 | Mark Tucker | 25 | 2017-2021 | |
| 26 | César González# | 24 | 2021-2023 | |
| 26 | Chris Hayes# | 24 | 2023-2027 | |
| 26 | Eric Patnode | 24 | 2016-2025 | |
| 29 | Jason Ackerman | 23 | 2015-2022 | |
| 29 | Álex Carrillo | 23 | 2018-2021 | |
| 29 | António Fabián# | 23 | 2020-2028 | |
| 29 | Ralph Haggerty# | 23 | 2027-2030 | |
| 29 | Homer O'Lannigan | 23 | 2018-2021 | |
| 29 | Hartmann Riedman# | 23 | 2024-2027 | |
| 29 | Alex Simmons | 23 | 2017-2024 | |
| 36 | Chris Burgess | 22 | 2022-2027 | |
| 36 | Atila Freska# | 22 | 2026-2028 | |
| 36 | Gerald Keller# | 22 | 2026-2029 | |
| 36 | Miguel López# | 22 | 2026-2028 | |
| 36 | Homer Shafer | 22 | 2015-2020 | |
| 36 | Ray Thibaut | 22 | 2015-2019 | |
| 36 | José Vargo# | 22 | 2022-2024 | |
| 36 | Steven Williams | 22 | 2015-2019 | |
| 36 | Yoriyoshi Yoshimura# | 22 | 2028-2030 | |
| 45 | Victor de Meij# | 21 | 2025-2030 | |
| 45 | Elmer García# | 21 | 2021-2028 | |
| 45 | Peter Hall# | 21 | 2024-2028 | |
| 45 | Mike Russell | 21 | 2018-2022 | |
| 45 | Maxwell Simon# | 21 | 2024-2027 | |
| 50 | Rhett Abbott# | 20 | 2029-2030 | |
| 50 | Xavier Andrade | 20 | 2017-2022 | |
| 50 | Emory Bryant | 20 | 2015-2019 | |
| 50 | Tom Hernández | 20 | 2016-2021 | |
| 50 | Delmar Llerena# | 20 | 2026-2030 | |
| 50 | Carlos Peret# | 20 | 2025-2028 | |
| 50 | Bartolo Ramírez# | 20 | 2019-2030 | |
| 50 | Wilson Vélez | 20 | 2016-2022 | |
| 58 | Ken Carter | 19 | 2015-2016 | |
| 58 | Joe Lynn | 19 | 2018-2023 | |
| 58 | Richard Meyer | 19 | 2017-2021 | |
| 58 | Paul Nance | 19 | 2015-2025 | |
| 58 | José Ortíz# | 19 | 2024-2026 | |
| 58 | Júlio Vázquez# | 19 | 2027-2030 | |
| 64 | Sid Brown# | 18 | 2017-2023 | |
| 64 | Freddy González | 18 | 2015-2020 | |
| 64 | Anthony Hanover | 18 | 2016-2020 | |
| 64 | Greg Kelly | 18 | 2016-2020 | |
| 64 | Érico Laborde# | 18 | 2029-2030 | |
| 64 | Alonso Rodríguez | 18 | 2015-2019 | |
| 64 | Jason Troughton# | 18 | 2023-2030 | |
| 64 | Orlando Uribe# | 18 | 2025-2030 | |
| 72 | Steve Bryan# | 17 | 2019-2030 | |
| 72 | Woody Carlson# | 17 | 2018-2020 | |
| 72 | Norberto Concepción# | 17 | 2027-2028 | |
| 72 | Luis Fernández | 17 | 2015-2024 | |
| 72 | King Fletcher# | 17 | 2020-2023 | |
| 72 | Doug Green# | 17 | 2018-2020 | |
| 72 | Jesús Guerra# | 17 | 2026-2028 | |
| 72 | Gabriel Herrera# | 17 | 2026-2028 | |
| 72 | Teddy Jones | 17 | 2017-2019 | |
| 72 | Oswaldo Mobray# | 17 | 2023-2024 | |
| 72 | Travis Nelson# | 17 | 2024-2029 | |
| 72 | Lindsay Novak# | 17 | 2024-2030 | |
| 72 | Aurelio Ornelas# | 17 | 2026-2030 | |
| 72 | José Rodríguez | 17 | 2015-2019 | |
| 72 | John Shirley | 17 | 2018-2025 | |
| 72 | Artie Taylor | 17 | 2017-2018 | |
| 72 | Eric Taylor | 17 | 2019-2021 | |
| 72 | Elroy Thompkins# | 17 | 2026-2027 | |
| 72 | José Trujillo | 17 | 2016-2019 | |
| 72 | Gabriel Valenzuela# | 17 | 2026-2029 | |
| 72 | Louis Webber | 17 | 2016-2019 | |
| 72 | Brad Wilson | 17 | 2015-2021 | |
| 94 | José Barajas# | 16 | 2022-2025 | |
| 94 | Nick Blount | 16 | 2016-2019 | |
| 94 | John Boyle | 16 | 2017-2022 | |
| 94 | Robert Byrd | 16 | 2017-2023 | |
| 94 | Iván Castillo | 16 | 2015-2018 | |
| 94 | Enrique Castro# | 16 | 2028-2028 | |
| 94 | Hubert Dunham | 16 | 2016-2027 |
