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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 | Salvador López# | 39 | 2029-2034 | |
| 3 | Mike Barrett | 37 | 2022-2027 | |
| 3 | Woo-suk Cho | 37 | 2026-2032 | |
| 5 | Nicolaas de Jongh# | 36 | 2031-2036 | |
| 6 | José Cabrera | 35 | 2025-2028 | |
| 7 | Jesús López | 33 | 2016-2023 | |
| 7 | Bob McGhee | 33 | 2015-2028 | |
| 7 | Pieter Spitsbaard | 33 | 2029-2036 | |
| 7 | John Wallbank# | 33 | 2030-2036 | |
| 11 | R.J. Anderson | 31 | 2020-2027 | |
| 11 | Stefan Famintsyn | 31 | 2033-2036 | |
| 11 | Manuel Medranda# | 31 | 2034-2037 | |
| 14 | Shawn Arnold | 30 | 2015-2022 | |
| 14 | William Bonner | 30 | 2020-2027 | |
| 14 | Louis McDowell | 30 | 2015-2030 | |
| 14 | Scott Mildren | 30 | 2024-2027 | |
| 14 | Cisco Ortíz | 30 | 2025-2030 | |
| 14 | Júlio Palácios | 30 | 2021-2026 | |
| 14 | Roberto Roque | 30 | 2030-2034 | |
| 21 | Josh Gardner | 29 | 2017-2021 | |
| 21 | Júlio Vázquez | 29 | 2027-2032 | |
| 23 | Paul Addison | 28 | 2027-2031 | |
| 23 | Clay Clark | 28 | 2015-2018 | |
| 23 | Min-chin Kim | 28 | 2030-2035 | |
| 26 | Chris Hughes# | 27 | 2033-2037 | |
| 26 | Brent Riley | 27 | 2015-2025 | |
| 28 | Travis Carson | 26 | 2020-2021 | |
| 28 | Daryl Keirl# | 26 | 2031-2035 | |
| 28 | Cisco Romero | 26 | 2019-2022 | |
| 28 | Pedro Romero | 26 | 2020-2026 | |
| 28 | Rob Smith | 26 | 2018-2027 | |
| 33 | Jorge Carrión | 25 | 2022-2026 | |
| 33 | Victor de Meij# | 25 | 2025-2032 | |
| 33 | Jeff Moore | 25 | 2020-2022 | |
| 33 | Santiago Ramírez# | 25 | 2030-2034 | |
| 33 | Javier Roldán | 25 | 2019-2023 | |
| 33 | César Soto# | 25 | 2033-2035 | |
| 33 | Sixto Soto | 25 | 2028-2034 | |
| 33 | Mark Tucker | 25 | 2017-2021 | |
| 41 | António Fernández# | 24 | 2033-2037 | |
| 41 | César González | 24 | 2021-2023 | |
| 41 | Chris Hayes | 24 | 2023-2027 | |
| 41 | Maximiano Mealha# | 24 | 2033-2037 | |
| 41 | César Morales# | 24 | 2035-2037 | |
| 41 | Seong-hyeon Pak | 24 | 2031-2035 | |
| 41 | Eric Patnode | 24 | 2016-2025 | |
| 48 | Jason Ackerman | 23 | 2015-2022 | |
| 48 | Álex Carrillo | 23 | 2018-2021 | |
| 48 | António Fabián | 23 | 2020-2028 | |
| 48 | Ralph Haggerty# | 23 | 2027-2030 | |
| 48 | Delmar Llerena | 23 | 2026-2032 | |
| 48 | Homer O'Lannigan | 23 | 2018-2021 | |
| 48 | Hartmann Riedman | 23 | 2024-2027 | |
| 48 | Alex Simmons | 23 | 2017-2024 | |
| 56 | Chris Burgess | 22 | 2022-2027 | |
| 56 | Atila Freska# | 22 | 2026-2028 | |
| 56 | Gerald Keller# | 22 | 2026-2029 | |
| 56 | Miguel López# | 22 | 2026-2028 | |
| 56 | Katsumoto Miyanohara# | 22 | 2029-2033 | |
| 56 | Homer Shafer | 22 | 2015-2020 | |
| 56 | Ray Thibaut | 22 | 2015-2019 | |
| 56 | Orlando Uribe | 22 | 2025-2031 | |
| 56 | José Vargo | 22 | 2022-2024 | |
| 56 | Steven Williams | 22 | 2015-2019 | |
| 56 | Yoriyoshi Yoshimura | 22 | 2028-2030 | |
| 67 | Mick Alston# | 21 | 2028-2036 | |
| 67 | Eurauraga Attunga# | 21 | 2034-2037 | |
| 67 | Loren Berdine | 21 | 2032-2034 | |
| 67 | José Blanco# | 21 | 2032-2034 | |
| 67 | Elmer García | 21 | 2021-2028 | |
| 67 | Peter Hall | 21 | 2024-2028 | |
| 67 | Andrew Holloway | 21 | 2028-2032 | |
| 67 | Jesús Lara# | 21 | 2030-2037 | |
| 67 | Grover Lowdermilk# | 21 | 2029-2033 | |
| 67 | Octávio Rodríguez | 21 | 2029-2032 | |
| 67 | Ángel Roldán | 21 | 2033-2036 | |
| 67 | Mike Russell | 21 | 2018-2022 | |
| 67 | Maxwell Simon | 21 | 2024-2027 | |
| 80 | Rhett Abbott# | 20 | 2029-2031 | |
| 80 | Xavier Andrade | 20 | 2017-2022 | |
| 80 | Emory Bryant | 20 | 2015-2019 | |
| 80 | Pleun Davidse | 20 | 2029-2035 | |
| 80 | Vladmiri Fanardjyan | 20 | 2030-2036 | |
| 80 | Dusty Fox# | 20 | 2033-2034 | |
| 80 | Tom Hernández | 20 | 2016-2021 | |
| 80 | Carlos Peret | 20 | 2025-2028 | |
| 80 | Bartolo Ramírez | 20 | 2019-2030 | |
| 80 | Cristóbal Román# | 20 | 2036-2037 | |
| 80 | Bru Sotelo | 20 | 2032-2034 | |
| 80 | Wilson Vélez | 20 | 2016-2022 | |
| 92 | Mark Bell | 19 | 2024-2031 | |
| 92 | Ken Carter | 19 | 2015-2016 | |
| 92 | Joe Lynn | 19 | 2018-2023 | |
| 92 | Ernesto Méndez# | 19 | 2036-2037 | |
| 92 | Richard Meyer | 19 | 2017-2021 | |
| 92 | Yoshi Minamoto# | 19 | 2030-2034 | |
| 92 | Paul Nance | 19 | 2015-2025 | |
| 92 | José Ortíz# | 19 | 2024-2026 | |
| 92 | Sam Pelsize# | 19 | 2030-2034 |
