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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 | Janghyun Han# | 88 | 2044-2057 | |
| 4 | Nathaniel Riley | 85 | 2016-2030 | |
| 5 | Rafael Cardona | 82 | 2022-2035 | |
| 6 | Jeff Hale | 81 | 2014-2027 | |
| 7 | Fernando Lujino# | 79 | 2042-2057 | |
| 7 | Nicholas Wells | 79 | 2019-2032 | |
| 9 | Travis Morgan | 78 | 2039-2049 | |
| 10 | Van Hileman# | 74 | 2041-2057 | |
| 10 | Eddie Kop* | 74 | 2023-2042 | |
| 12 | Jay Newton | 73 | 2042-2054 | |
| 13 | Gregory Collins# | 72 | 2045-2057 | |
| 14 | Howard Randolph# | 71 | 2048-2057 | |
| 14 | Gustavo Tobías | 71 | 2032-2044 | |
| 16 | Pedro Valdéz | 68 | 2020-2040 | |
| 17 | Robbie Baxter | 64 | 2022-2037 | |
| 17 | Virgil Dickerson | 64 | 2043-2054 | |
| 19 | Javier Mora | 63 | 2020-2034 | |
| 20 | Walt Coffman* | 61 | 2026-2038 | |
| 21 | Wes Hamm* | 60 | 2021-2037 | |
| 22 | Héctor Alarcon | 57 | 2015-2027 | |
| 22 | Paul Díaz | 57 | 2019-2030 | |
| 24 | Wayne Craig | 56 | 2015-2023 | |
| 24 | Matthew Fallows | 56 | 2034-2048 | |
| 24 | Paul Haines | 56 | 2038-2052 | |
| 27 | Manuel Martínez# | 55 | 2048-2057 | |
| 27 | Jesús Vidro* | 55 | 2033-2045 | |
| 27 | Allen Yohemas | 55 | 2022-2031 | |
| 30 | Anastasio Cabanillas Jr. | 54 | 2037-2046 | |
| 30 | Andy Coker | 54 | 2016-2026 | |
| 30 | Wayne Hurst | 54 | 2015-2028 | |
| 30 | David Moore | 54 | 2034-2046 | |
| 34 | Aaron Daniels# | 53 | 2048-2055 | |
| 34 | Juan Moreno | 53 | 2037-2045 | |
| 34 | Domingo Ramírez | 53 | 2022-2039 | |
| 34 | César Sandoval | 53 | 2038-2048 | |
| 38 | Jason Kofod# | 52 | 2051-2057 | |
| 39 | Kevin Brown# | 50 | 2050-2057 | |
| 40 | Pedro Castro | 49 | 2018-2032 | |
| 40 | Jong-yong Ha | 49 | 2038-2051 | |
| 40 | Stanford McCain | 49 | 2031-2041 | |
| 43 | Dave Becker | 48 | 2040-2054 | |
| 43 | Chip Bishop | 48 | 2018-2028 | |
| 43 | Allen Blair | 48 | 2015-2032 | |
| 43 | Chase Davis# | 48 | 2049-2056 | |
| 43 | Urs Ehles | 48 | 2036-2051 | |
| 43 | Kyle Horton | 48 | 2047-2056 | |
| 43 | Tyler MacHugh | 48 | 2023-2033 | |
| 43 | Bobby Swain | 48 | 2020-2031 | |
| 43 | John Wilkins* | 48 | 2015-2026 | |
| 43 | Stanley Yelnats | 48 | 2030-2038 | |
| 53 | Sidney Petty# | 47 | 2048-2056 | |
| 54 | John Braun | 46 | 2014-2022 | |
| 54 | Craig Fitzgerald | 46 | 2036-2050 | |
| 54 | John Holley | 46 | 2014-2022 | |
| 54 | Roderick Rhodes | 46 | 2017-2028 | |
| 54 | Noud Taaij# | 46 | 2047-2057 | |
| 59 | Pat Butler# | 45 | 2045-2056 | |
| 59 | Anatoly Ivanovich | 45 | 2030-2039 | |
| 59 | Aurelio López | 45 | 2022-2037 | |
| 62 | Andrew Johnson# | 44 | 2046-2057 | |
| 62 | Zhao-ji Qiu | 44 | 2036-2044 | |
| 62 | Sylvain Richard | 44 | 2042-2054 | |
| 65 | Truman Valentine | 43 | 2022-2031 | |
| 66 | Faisal bin Nabeel | 42 | 2034-2041 | |
| 66 | Ratko Davidovic | 42 | 2035-2043 | |
| 66 | Juan Díaz | 42 | 2025-2036 | |
| 66 | Vincent Hall | 42 | 2021-2031 | |
| 66 | Ralph McKinney* | 42 | 2019-2034 | |
| 66 | Arnie Pittman | 42 | 2022-2030 | |
| 66 | Chase Sims | 42 | 2039-2049 | |
| 73 | Bailey Borrett | 41 | 2043-2052 | |
| 73 | Boris Milatovic | 41 | 2042-2057 | |
| 73 | Jorge Otero* | 41 | 2030-2040 | |
| 73 | Jorge Souza# | 41 | 2042-2057 | |
| 77 | Heath Brown | 40 | 2043-2053 | |
| 77 | Kevin Nogilny* | 40 | 2032-2046 | |
| 77 | Joe Pruitt | 40 | 2031-2039 | |
| 77 | Armando Romano | 40 | 2029-2042 | |
| 77 | Juan Torres | 40 | 2021-2032 | |
| 82 | Henry Hall | 39 | 2015-2026 | |
| 82 | John Rigsby | 39 | 2034-2047 | |
| 82 | Luis Torres | 39 | 2024-2035 | |
| 82 | Brewster Warble | 39 | 2031-2046 | |
| 86 | Gary Ashley | 38 | 2034-2048 | |
| 86 | Michael Battle | 38 | 2017-2021 | |
| 86 | Tommaso Cugnoni# | 38 | 2046-2057 | |
| 86 | George Frazier | 38 | 2017-2036 | |
| 86 | Chris Holland | 38 | 2035-2045 | |
| 86 | Kyuichi Hori | 38 | 2031-2042 | |
| 86 | Ton Jobse | 38 | 2031-2045 | |
| 86 | Lynwood Matos | 38 | 2021-2031 | |
| 86 | Guillermo Pérez | 38 | 2015-2025 | |
| 95 | Craig Culver# | 37 | 2047-2057 | |
| 95 | Pat Horton | 37 | 2014-2019 | |
| 95 | José Martínez# | 37 | 2049-2057 | |
| 95 | Roger Rodenburg | 37 | 2036-2044 | |
| 95 | Cory Sanders | 37 | 2021-2036 | |
| 95 | Alex Thompson# | 37 | 2054-2057 |
