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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Juan Guillén* | 112 | 2027-2039 | |
| 2 | Bartolomeu Lio | 89 | 2019-2034 | |
| 3 | Nathaniel Riley | 85 | 2016-2030 | |
| 4 | Rafael Cardona | 82 | 2022-2035 | |
| 5 | Jeff Hale | 81 | 2014-2027 | |
| 6 | Nicholas Wells | 79 | 2019-2032 | |
| 7 | Janghyun Han# | 78 | 2044-2053 | |
| 7 | Travis Morgan | 78 | 2039-2049 | |
| 9 | Fernando Lujino# | 77 | 2042-2054 | |
| 10 | Eddie Kop* | 74 | 2023-2042 | |
| 11 | Jay Newton# | 73 | 2042-2054 | |
| 12 | Gustavo Tobías | 71 | 2032-2044 | |
| 13 | Pedro Valdéz | 68 | 2020-2040 | |
| 14 | Robbie Baxter | 64 | 2022-2037 | |
| 14 | Virgil Dickerson# | 64 | 2043-2054 | |
| 16 | Javier Mora | 63 | 2020-2034 | |
| 17 | Howard Randolph# | 62 | 2048-2054 | |
| 18 | Walt Coffman* | 61 | 2026-2038 | |
| 19 | Wes Hamm* | 60 | 2021-2037 | |
| 20 | Van Hileman# | 59 | 2041-2054 | |
| 21 | Héctor Alarcon | 57 | 2015-2027 | |
| 21 | Paul Díaz | 57 | 2019-2030 | |
| 23 | Wayne Craig | 56 | 2015-2023 | |
| 23 | Matthew Fallows | 56 | 2034-2048 | |
| 23 | Paul Haines | 56 | 2038-2052 | |
| 26 | Jesús Vidro | 55 | 2033-2045 | |
| 26 | Allen Yohemas | 55 | 2022-2031 | |
| 28 | Anastasio Cabanillas Jr. | 54 | 2037-2046 | |
| 28 | Andy Coker | 54 | 2016-2026 | |
| 28 | Wayne Hurst | 54 | 2015-2028 | |
| 28 | David Moore | 54 | 2034-2046 | |
| 32 | Juan Moreno | 53 | 2037-2045 | |
| 32 | Domingo Ramírez | 53 | 2022-2039 | |
| 32 | César Sandoval | 53 | 2038-2048 | |
| 35 | Pedro Castro | 49 | 2018-2032 | |
| 35 | Jong-yong Ha | 49 | 2038-2051 | |
| 35 | Stanford McCain | 49 | 2031-2041 | |
| 38 | Dave Becker# | 48 | 2040-2054 | |
| 38 | Chip Bishop | 48 | 2018-2028 | |
| 38 | Allen Blair | 48 | 2015-2032 | |
| 38 | Gregory Collins# | 48 | 2045-2054 | |
| 38 | Urs Ehles | 48 | 2036-2051 | |
| 38 | Tyler MacHugh | 48 | 2023-2033 | |
| 38 | Bobby Swain | 48 | 2020-2031 | |
| 38 | John Wilkins* | 48 | 2015-2026 | |
| 38 | Stanley Yelnats | 48 | 2030-2038 | |
| 47 | John Braun | 46 | 2014-2022 | |
| 47 | Craig Fitzgerald | 46 | 2036-2050 | |
| 47 | John Holley | 46 | 2014-2022 | |
| 47 | Manuel Martínez# | 46 | 2048-2054 | |
| 47 | Roderick Rhodes | 46 | 2017-2028 | |
| 52 | Pat Butler# | 45 | 2045-2054 | |
| 52 | Anatoly Ivanovich | 45 | 2030-2039 | |
| 52 | Aurelio López | 45 | 2022-2037 | |
| 55 | Zhao-ji Qiu | 44 | 2036-2044 | |
| 55 | Sylvain Richard | 44 | 2042-2054 | |
| 57 | Aaron Daniels# | 43 | 2048-2054 | |
| 57 | Truman Valentine | 43 | 2022-2031 | |
| 59 | Faisal bin Nabeel | 42 | 2034-2041 | |
| 59 | Ratko Davidovic | 42 | 2035-2043 | |
| 59 | Juan Díaz | 42 | 2025-2036 | |
| 59 | Vincent Hall | 42 | 2021-2031 | |
| 59 | Ralph McKinney* | 42 | 2019-2034 | |
| 59 | Arnie Pittman | 42 | 2022-2030 | |
| 59 | Chase Sims | 42 | 2039-2049 | |
| 66 | Bailey Borrett | 41 | 2043-2052 | |
| 66 | Jorge Otero* | 41 | 2030-2040 | |
| 68 | Heath Brown# | 40 | 2043-2053 | |
| 68 | Chase Davis# | 40 | 2049-2053 | |
| 68 | Kevin Nogilny | 40 | 2032-2046 | |
| 68 | Joe Pruitt | 40 | 2031-2039 | |
| 68 | Armando Romano | 40 | 2029-2042 | |
| 68 | Juan Torres | 40 | 2021-2032 | |
| 74 | Henry Hall | 39 | 2015-2026 | |
| 74 | Sidney Petty# | 39 | 2048-2052 | |
| 74 | John Rigsby | 39 | 2034-2047 | |
| 74 | Luis Torres | 39 | 2024-2035 | |
| 74 | Brewster Warble | 39 | 2031-2046 | |
| 79 | Gary Ashley | 38 | 2034-2048 | |
| 79 | Michael Battle | 38 | 2017-2021 | |
| 79 | Tommaso Cugnoni# | 38 | 2046-2053 | |
| 79 | George Frazier | 38 | 2017-2036 | |
| 79 | Chris Holland | 38 | 2035-2045 | |
| 79 | Kyuichi Hori | 38 | 2031-2042 | |
| 79 | Ton Jobse | 38 | 2031-2045 | |
| 79 | Lynwood Matos | 38 | 2021-2031 | |
| 79 | Guillermo Pérez | 38 | 2015-2025 | |
| 88 | Kevin Brown# | 37 | 2050-2054 | |
| 88 | Pat Horton | 37 | 2014-2019 | |
| 88 | Boris Milatovic# | 37 | 2042-2053 | |
| 88 | Roger Rodenburg | 37 | 2036-2044 | |
| 88 | Cory Sanders | 37 | 2021-2036 | |
| 88 | Brantford Winstworth III | 37 | 2029-2043 | |
| 88 | Yin-zhen Wu | 37 | 2043-2050 | |
| 95 | Kyle Horton# | 36 | 2047-2054 | |
| 95 | Jeff Mahl | 36 | 2035-2046 | |
| 95 | António Marés | 36 | 2024-2031 | |
| 95 | António Muñóz | 36 | 2029-2039 | |
| 99 | Manuel Delgadillo | 35 | 2028-2038 | |
| 99 | Ralph DePalma | 35 | 2036-2047 |
