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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Victor Brey | 72 | 2021-2028 | |
| 2 | Willie Cameron | 54 | 2016-2031 | |
| 3 | Patrick Ibáñez# | 46 | 2035-2046 | |
| 4 | Matt Davenport | 45 | 2029-2037 | |
| 5 | Luis Hernández | 43 | 2030-2037 | |
| 5 | Cisco Pérez | 43 | 2034-2038 | |
| 7 | Wop Baars | 41 | 2032-2041 | |
| 7 | Drew Cullen | 41 | 2027-2035 | |
| 9 | Mario Ruíz | 39 | 2023-2031 | |
| 10 | Miguel Cervantes | 38 | 2026-2038 | |
| 10 | Chae-seong Kim | 38 | 2023-2033 | |
| 10 | Giovanni Mireles | 38 | 2026-2045 | |
| 13 | Salvador Sagastizabal | 37 | 2036-2043 | |
| 14 | Claudio Díaz | 35 | 2022-2031 | |
| 14 | José Salinas | 35 | 2017-2027 | |
| 14 | Javier Soto | 35 | 2040-2044 | |
| 17 | Francisco Barrios | 34 | 2020-2033 | |
| 17 | Marvin Mangin | 34 | 2023-2028 | |
| 17 | Marvin Stevens# | 34 | 2043-2047 | |
| 20 | Danny Byrd# | 33 | 2044-2047 | |
| 20 | Miguel Cabañas | 33 | 2029-2035 | |
| 20 | Dan Dunn# | 33 | 2042-2047 | |
| 20 | Fred Gunther | 33 | 2036-2040 | |
| 20 | Nick Hayes# | 33 | 2041-2047 | |
| 25 | Roy Alsobrook | 32 | 2028-2038 | |
| 25 | Alejandro Araya | 32 | 2028-2039 | |
| 25 | Dennis Brown | 32 | 2022-2030 | |
| 25 | Earl Brown | 32 | 2023-2031 | |
| 25 | Antonio Godfrey | 32 | 2028-2033 | |
| 25 | António López# | 32 | 2041-2047 | |
| 25 | Shunen Takahashi | 32 | 2022-2035 | |
| 25 | Miguel Álvarez | 32 | 2027-2033 | |
| 33 | Jorge Cedeño | 31 | 2033-2037 | |
| 33 | Steve Costlow | 31 | 2032-2038 | |
| 33 | King Fletcher | 31 | 2023-2030 | |
| 33 | Artie Horton | 31 | 2022-2025 | |
| 33 | Louis McDowell | 31 | 2016-2028 | |
| 33 | José Ortíz | 31 | 2026-2037 | |
| 33 | Larry Strozier | 31 | 2030-2035 | |
| 33 | Joel Walden | 31 | 2036-2043 | |
| 33 | Won-u Yi | 31 | 2029-2041 | |
| 42 | Raúl Andrés | 30 | 2016-2021 | |
| 42 | Emerson Horton | 30 | 2039-2044 | |
| 42 | Jason Huggins | 30 | 2037-2046 | |
| 42 | Dahab Kanda | 30 | 2029-2043 | |
| 42 | Liam Thomson | 30 | 2032-2044 | |
| 42 | Bob Warford | 30 | 2018-2034 | |
| 48 | Lucas Begay | 29 | 2025-2028 | |
| 48 | Roberto Calderón | 29 | 2024-2035 | |
| 48 | Arturo Guerrero | 29 | 2028-2039 | |
| 48 | José Guillén | 29 | 2028-2030 | |
| 48 | Roberto Gómez | 29 | 2022-2031 | |
| 48 | Cris Herrera | 29 | 2022-2034 | |
| 48 | Sammy Nash | 29 | 2024-2029 | |
| 48 | Scott Thompson | 29 | 2035-2038 | |
| 48 | Octávio Valdéz | 29 | 2033-2039 | |
| 57 | Frank Bryant | 28 | 2021-2028 | |
| 57 | Benjamin Busto | 28 | 2029-2038 | |
| 57 | Hervé Favier | 28 | 2028-2043 | |
| 57 | Ollie McDaniell | 28 | 2033-2037 | |
| 57 | Bobby Roode | 28 | 2031-2041 | |
| 57 | Doug Ryan | 28 | 2016-2024 | |
| 57 | Albert Sierra | 28 | 2034-2041 | |
| 64 | Gary Barber | 27 | 2021-2033 | |
| 64 | Eduardo Capata | 27 | 2019-2032 | |
| 64 | Jordan Coffey | 27 | 2035-2043 | |
| 64 | Hank Downey | 27 | 2021-2030 | |
| 64 | Carlos Díaz | 27 | 2030-2033 | |
| 64 | Norberto Flores | 27 | 2027-2033 | |
| 64 | Aurélien Godet | 27 | 2015-2023 | |
| 64 | Ralph Haggerty | 27 | 2029-2038 | |
| 64 | Ben Hopley | 27 | 2024-2034 | |
| 64 | Zuo-lin Liang# | 27 | 2040-2047 | |
| 64 | José Marín | 27 | 2034-2041 | |
| 64 | Emil Olsson | 27 | 2027-2036 | |
| 64 | Harvey Wyles# | 27 | 2038-2047 | |
| 64 | Gerrit Zuidgeest | 27 | 2035-2040 | |
| 78 | José Acevedo | 26 | 2013-2023 | |
| 78 | Norm Burris | 26 | 2016-2021 | |
| 78 | Logan Gregory | 26 | 2027-2035 | |
| 78 | Kabeya Kasongo# | 26 | 2034-2038 | |
| 78 | Arturo Mesa | 26 | 2037-2040 | |
| 78 | Silverberry Mouhon | 26 | 2035-2043 | |
| 78 | Harry Stuterberg# | 26 | 2034-2047 | |
| 78 | Ricardo Suárez | 26 | 2027-2032 | |
| 86 | Félix Aiza | 25 | 2041-2045 | |
| 86 | Anastasio Cabanillas Jr.# | 25 | 2033-2036 | |
| 86 | Woo-suk Cho | 25 | 2031-2035 | |
| 86 | Roberto De La Cruz | 25 | 2024-2027 | |
| 86 | Wayne Downey | 25 | 2022-2025 | |
| 86 | Ray Goolsby | 25 | 2031-2045 | |
| 86 | Travis Grant | 25 | 2024-2034 | |
| 86 | Guillermo Guerrero | 25 | 2037-2046 | |
| 86 | Tony Hernández | 25 | 2016-2020 | |
| 86 | Claude Khatoon# | 25 | 2042-2047 | |
| 86 | Pedro Lara | 25 | 2025-2028 | |
| 86 | Yoshi Minamoto | 25 | 2032-2036 | |
| 86 | Doruk Oyan | 25 | 2016-2018 | |
| 86 | Timoteo Sassetti | 25 | 2038-2044 | |
| 86 | Brian Scalabrine | 25 | 2027-2032 |
