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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 | Marvin Stevens | 55 | 2043-2056 | |
| 3 | Willie Cameron | 54 | 2016-2031 | |
| 4 | Noboru Kokawa# | 48 | 2048-2054 | |
| 5 | Ikaia Duncalf | 47 | 2045-2054 | |
| 6 | Patrick Ibáñez | 46 | 2035-2046 | |
| 7 | Matt Davenport | 45 | 2029-2037 | |
| 7 | António López | 45 | 2041-2050 | |
| 9 | Danny Byrd | 43 | 2044-2050 | |
| 9 | Luis Hernández | 43 | 2030-2037 | |
| 9 | Cisco Pérez | 43 | 2034-2038 | |
| 12 | Mario Silva | 42 | 2042-2055 | |
| 13 | Wop Baars | 41 | 2032-2041 | |
| 13 | Drew Cullen | 41 | 2027-2035 | |
| 15 | Mario Ruíz | 39 | 2023-2031 | |
| 16 | Miguel Cervantes | 38 | 2026-2038 | |
| 16 | Chae-seong Kim | 38 | 2023-2033 | |
| 16 | Giovanni Mireles | 38 | 2026-2045 | |
| 19 | Salvador Sagastizabal | 37 | 2036-2043 | |
| 20 | Claudio Díaz | 35 | 2022-2031 | |
| 20 | Edmund Rochefort# | 35 | 2050-2056 | |
| 20 | José Salinas | 35 | 2017-2027 | |
| 20 | Javier Soto | 35 | 2040-2044 | |
| 20 | Chin-yau Tu# | 35 | 2047-2056 | |
| 25 | Francisco Barrios | 34 | 2020-2033 | |
| 25 | Marvin Mangin | 34 | 2023-2028 | |
| 25 | Andrew Shoemaker# | 34 | 2049-2055 | |
| 28 | Miguel Cabañas | 33 | 2029-2035 | |
| 28 | Dan Dunn | 33 | 2042-2047 | |
| 28 | Fred Gunther | 33 | 2036-2040 | |
| 28 | Nick Hayes | 33 | 2041-2047 | |
| 28 | Jing-quo Ts'ai# | 33 | 2052-2056 | |
| 33 | Roy Alsobrook | 32 | 2028-2038 | |
| 33 | Alejandro Araya | 32 | 2028-2039 | |
| 33 | Dennis Brown | 32 | 2022-2030 | |
| 33 | Earl Brown | 32 | 2023-2031 | |
| 33 | Jimmy Evans | 32 | 2043-2049 | |
| 33 | Antonio Godfrey | 32 | 2028-2033 | |
| 33 | Claude Khatoon | 32 | 2042-2048 | |
| 33 | Shunen Takahashi | 32 | 2022-2035 | |
| 33 | Miguel Álvarez | 32 | 2027-2033 | |
| 42 | Jorge Cedeño | 31 | 2033-2037 | |
| 42 | Steve Costlow | 31 | 2032-2038 | |
| 42 | King Fletcher | 31 | 2023-2030 | |
| 42 | Artie Horton | 31 | 2022-2025 | |
| 42 | Hunter Kirkland# | 31 | 2046-2056 | |
| 42 | Louis McDowell | 31 | 2016-2028 | |
| 42 | Dan McIntyre# | 31 | 2049-2056 | |
| 42 | José Ortíz | 31 | 2026-2037 | |
| 42 | Arthur Stevenson | 31 | 2046-2054 | |
| 42 | Larry Strozier | 31 | 2030-2035 | |
| 42 | Joel Walden | 31 | 2036-2043 | |
| 42 | Won-u Yi | 31 | 2029-2041 | |
| 54 | Raúl Andrés | 30 | 2016-2021 | |
| 54 | Cecil Drabek | 30 | 2043-2051 | |
| 54 | Emerson Horton | 30 | 2039-2044 | |
| 54 | Jason Huggins | 30 | 2037-2046 | |
| 54 | Dahab Kanda | 30 | 2029-2043 | |
| 54 | Raúl Martínez# | 30 | 2048-2056 | |
| 54 | Liam Thomson | 30 | 2032-2044 | |
| 54 | Bob Warford | 30 | 2018-2034 | |
| 62 | Lucas Begay | 29 | 2025-2028 | |
| 62 | Roberto Calderón | 29 | 2024-2035 | |
| 62 | Robert Carlson# | 29 | 2053-2056 | |
| 62 | Arturo Guerrero | 29 | 2028-2039 | |
| 62 | José Guillén | 29 | 2028-2030 | |
| 62 | Roberto Gómez | 29 | 2022-2031 | |
| 62 | Cris Herrera | 29 | 2022-2034 | |
| 62 | Vic Lee# | 29 | 2049-2056 | |
| 62 | John McGrath# | 29 | 2054-2056 | |
| 62 | Sammy Nash | 29 | 2024-2029 | |
| 62 | Scott Thompson | 29 | 2035-2038 | |
| 62 | Mike Thornton# | 29 | 2051-2054 | |
| 62 | Octávio Valdéz | 29 | 2033-2039 | |
| 75 | Frank Bryant | 28 | 2021-2028 | |
| 75 | Benjamin Busto | 28 | 2029-2038 | |
| 75 | Hervé Favier | 28 | 2028-2043 | |
| 75 | Ollie McDaniell | 28 | 2033-2037 | |
| 75 | Bobby Roode | 28 | 2031-2041 | |
| 75 | Doug Ryan | 28 | 2016-2024 | |
| 75 | Albert Sierra | 28 | 2034-2041 | |
| 82 | Gary Barber | 27 | 2021-2033 | |
| 82 | Eduardo Capata | 27 | 2019-2032 | |
| 82 | Anthony Carney# | 27 | 2048-2050 | |
| 82 | Jordan Coffey | 27 | 2035-2043 | |
| 82 | Hank Downey | 27 | 2021-2030 | |
| 82 | Carlos Díaz | 27 | 2030-2033 | |
| 82 | Norberto Flores | 27 | 2027-2033 | |
| 82 | Aurélien Godet | 27 | 2015-2023 | |
| 82 | Steve Gourin# | 27 | 2054-2056 | |
| 82 | Ralph Haggerty | 27 | 2029-2038 | |
| 82 | Ben Hopley | 27 | 2024-2034 | |
| 82 | Zuo-lin Liang | 27 | 2040-2047 | |
| 82 | José Marín | 27 | 2034-2041 | |
| 82 | Homer Mathis# | 27 | 2053-2056 | |
| 82 | Emil Olsson | 27 | 2027-2036 | |
| 82 | Harvey Wyles | 27 | 2038-2047 | |
| 82 | Steve Young | 27 | 2042-2049 | |
| 82 | Gerrit Zuidgeest | 27 | 2035-2040 | |
| 100 | José Acevedo | 26 | 2013-2023 |
