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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 | Salvador López# | 33 | 2029-2033 | |
| 5 | Bob McGhee | 33 | 2015-2028 | |
| 8 | R.J. Anderson | 31 | 2020-2027 | |
| 9 | Shawn Arnold | 30 | 2015-2022 | |
| 9 | William Bonner | 30 | 2020-2027 | |
| 9 | Louis McDowell | 30 | 2015-2030 | |
| 9 | Scott Mildren# | 30 | 2024-2027 | |
| 9 | Cisco Ortíz# | 30 | 2025-2030 | |
| 9 | Júlio Palácios | 30 | 2021-2026 | |
| 15 | Josh Gardner | 29 | 2017-2021 | |
| 15 | 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 | |
| 20 | Pieter Spitsbaard# | 26 | 2029-2033 | |
| 25 | Jorge Carrión | 25 | 2022-2026 | |
| 25 | Victor de Meij# | 25 | 2025-2032 | |
| 25 | Jeff Moore | 25 | 2020-2022 | |
| 25 | Javier Roldán# | 25 | 2019-2023 | |
| 25 | Mark Tucker | 25 | 2017-2021 | |
| 30 | César González | 24 | 2021-2023 | |
| 30 | Chris Hayes# | 24 | 2023-2027 | |
| 30 | Eric Patnode | 24 | 2016-2025 | |
| 30 | Sixto Soto# | 24 | 2028-2033 | |
| 34 | Jason Ackerman | 23 | 2015-2022 | |
| 34 | Álex Carrillo | 23 | 2018-2021 | |
| 34 | António Fabián# | 23 | 2020-2028 | |
| 34 | Ralph Haggerty# | 23 | 2027-2030 | |
| 34 | Delmar Llerena# | 23 | 2026-2032 | |
| 34 | Homer O'Lannigan | 23 | 2018-2021 | |
| 34 | Hartmann Riedman# | 23 | 2024-2027 | |
| 34 | Alex Simmons | 23 | 2017-2024 | |
| 42 | Chris Burgess | 22 | 2022-2027 | |
| 42 | Atila Freska# | 22 | 2026-2028 | |
| 42 | Gerald Keller# | 22 | 2026-2029 | |
| 42 | Miguel López# | 22 | 2026-2028 | |
| 42 | Katsumoto Miyanohara# | 22 | 2029-2033 | |
| 42 | Homer Shafer | 22 | 2015-2020 | |
| 42 | Ray Thibaut | 22 | 2015-2019 | |
| 42 | Orlando Uribe# | 22 | 2025-2031 | |
| 42 | José Vargo# | 22 | 2022-2024 | |
| 42 | Steven Williams | 22 | 2015-2019 | |
| 42 | Yoriyoshi Yoshimura# | 22 | 2028-2030 | |
| 53 | Elmer García | 21 | 2021-2028 | |
| 53 | Peter Hall | 21 | 2024-2028 | |
| 53 | Andrew Holloway# | 21 | 2028-2032 | |
| 53 | Grover Lowdermilk# | 21 | 2029-2033 | |
| 53 | Octávio Rodríguez# | 21 | 2029-2032 | |
| 53 | Mike Russell | 21 | 2018-2022 | |
| 53 | Maxwell Simon | 21 | 2024-2027 | |
| 60 | Rhett Abbott# | 20 | 2029-2031 | |
| 60 | Xavier Andrade | 20 | 2017-2022 | |
| 60 | Emory Bryant | 20 | 2015-2019 | |
| 60 | Tom Hernández | 20 | 2016-2021 | |
| 60 | Carlos Peret# | 20 | 2025-2028 | |
| 60 | Bartolo Ramírez# | 20 | 2019-2030 | |
| 60 | Roberto Roque# | 20 | 2030-2033 | |
| 60 | Wilson Vélez | 20 | 2016-2022 | |
| 68 | Mark Bell# | 19 | 2024-2031 | |
| 68 | Ken Carter | 19 | 2015-2016 | |
| 68 | Joe Lynn | 19 | 2018-2023 | |
| 68 | Richard Meyer | 19 | 2017-2021 | |
| 68 | Paul Nance | 19 | 2015-2025 | |
| 68 | José Ortíz# | 19 | 2024-2026 | |
| 74 | Sima Babic# | 18 | 2031-2032 | |
| 74 | Sid Brown | 18 | 2017-2023 | |
| 74 | Steve Bryan | 18 | 2019-2031 | |
| 74 | Freddy González | 18 | 2015-2020 | |
| 74 | Anthony Hanover | 18 | 2016-2020 | |
| 74 | Gabriel Herrera# | 18 | 2026-2032 | |
| 74 | Pedro Herrera# | 18 | 2030-2032 | |
| 74 | Behar Jusufi# | 18 | 2029-2033 | |
| 74 | Greg Kelly | 18 | 2016-2020 | |
| 74 | Érico Laborde# | 18 | 2029-2030 | |
| 74 | Yoshi Minamoto# | 18 | 2030-2033 | |
| 74 | Vincent O'Higgin# | 18 | 2029-2031 | |
| 74 | Sam Pelsize# | 18 | 2030-2033 | |
| 74 | Alonso Rodríguez | 18 | 2015-2019 | |
| 74 | Ángelo Román | 18 | 2027-2032 | |
| 74 | Jason Troughton# | 18 | 2023-2030 | |
| 90 | Alain Arnaud# | 17 | 2029-2031 | |
| 90 | Rafael Bernal# | 17 | 2031-2033 | |
| 90 | Anastasio Cabanillas Jr.# | 17 | 2031-2033 | |
| 90 | Woody Carlson# | 17 | 2018-2020 | |
| 90 | Norberto Concepción# | 17 | 2027-2028 | |
| 90 | Luis Fernández | 17 | 2015-2024 | |
| 90 | King Fletcher | 17 | 2020-2023 | |
| 90 | Doug Green# | 17 | 2018-2020 | |
| 90 | Jesús Guerra# | 17 | 2026-2028 | |
| 90 | Teddy Jones | 17 | 2017-2019 | |
| 90 | Min-chin Kim# | 17 | 2030-2033 |
