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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 | Fernando Lujino | 99 | 2042-2060 | |
| 3 | Bartolomeu Lio | 89 | 2019-2034 | |
| 4 | Janghyun Han# | 88 | 2044-2062 | |
| 5 | Nathaniel Riley | 85 | 2016-2030 | |
| 6 | Howard Randolph# | 84 | 2048-2060 | |
| 7 | Gregory Collins | 83 | 2045-2062 | |
| 8 | Rafael Cardona | 82 | 2022-2035 | |
| 9 | Jeff Hale | 81 | 2014-2027 | |
| 10 | Nicholas Wells | 79 | 2019-2032 | |
| 11 | Travis Morgan | 78 | 2039-2049 | |
| 12 | Van Hileman* | 76 | 2041-2058 | |
| 13 | Eddie Kop* | 74 | 2023-2042 | |
| 14 | Jay Newton | 73 | 2042-2054 | |
| 15 | Gustavo Tobías | 71 | 2032-2044 | |
| 16 | Jason Kofod# | 70 | 2051-2062 | |
| 17 | Pedro Valdéz | 68 | 2020-2040 | |
| 18 | Robbie Baxter | 64 | 2022-2037 | |
| 18 | Virgil Dickerson | 64 | 2043-2054 | |
| 18 | Noud Taaij# | 64 | 2047-2063 | |
| 21 | Javier Mora | 63 | 2020-2034 | |
| 22 | Walt Coffman* | 61 | 2026-2038 | |
| 23 | Wes Hamm* | 60 | 2021-2037 | |
| 23 | Tom Johnston# | 60 | 2053-2062 | |
| 25 | Pat Butler# | 58 | 2045-2062 | |
| 26 | Héctor Alarcon | 57 | 2015-2027 | |
| 26 | Paul Díaz | 57 | 2019-2030 | |
| 28 | Wayne Craig | 56 | 2015-2023 | |
| 28 | Chase Davis | 56 | 2049-2061 | |
| 28 | Matthew Fallows | 56 | 2034-2048 | |
| 28 | Paul Haines | 56 | 2038-2052 | |
| 32 | Manuel Martínez | 55 | 2048-2057 | |
| 32 | Jesús Vidro* | 55 | 2033-2045 | |
| 32 | Allen Yohemas | 55 | 2022-2031 | |
| 35 | Anastasio Cabanillas Jr. | 54 | 2037-2046 | |
| 35 | Andy Coker | 54 | 2016-2026 | |
| 35 | Wayne Hurst | 54 | 2015-2028 | |
| 35 | David Moore | 54 | 2034-2046 | |
| 39 | Aaron Daniels# | 53 | 2048-2055 | |
| 39 | Juan Moreno | 53 | 2037-2045 | |
| 39 | Domingo Ramírez | 53 | 2022-2039 | |
| 39 | César Sandoval | 53 | 2038-2048 | |
| 43 | Clemenz Lawrence# | 52 | 2052-2061 | |
| 43 | Guy Riggs# | 52 | 2051-2062 | |
| 45 | Kevin Brown# | 51 | 2050-2060 | |
| 45 | Jorge Souza | 51 | 2042-2058 | |
| 45 | Miguel Velázquez# | 51 | 2051-2062 | |
| 48 | Pedro Castro | 49 | 2018-2032 | |
| 48 | Jong-yong Ha | 49 | 2038-2051 | |
| 48 | Stanford McCain | 49 | 2031-2041 | |
| 51 | Dave Becker | 48 | 2040-2054 | |
| 51 | Chip Bishop | 48 | 2018-2028 | |
| 51 | Allen Blair | 48 | 2015-2032 | |
| 51 | Urs Ehles | 48 | 2036-2051 | |
| 51 | Kyle Horton | 48 | 2047-2056 | |
| 51 | Tyler MacHugh | 48 | 2023-2033 | |
| 51 | Bobby Swain | 48 | 2020-2031 | |
| 51 | John Wilkins* | 48 | 2015-2026 | |
| 51 | Stanley Yelnats | 48 | 2030-2038 | |
| 60 | Al Ivey# | 47 | 2058-2062 | |
| 60 | Sidney Petty | 47 | 2048-2056 | |
| 62 | John Braun | 46 | 2014-2022 | |
| 62 | Craig Fitzgerald | 46 | 2036-2050 | |
| 62 | John Holley | 46 | 2014-2022 | |
| 62 | Roderick Rhodes | 46 | 2017-2028 | |
| 66 | Juan Cruz# | 45 | 2057-2061 | |
| 66 | Eddie Daniel# | 45 | 2053-2062 | |
| 66 | Anatoly Ivanovich | 45 | 2030-2039 | |
| 66 | Aurelio López | 45 | 2022-2037 | |
| 66 | Nick Snyder# | 45 | 2048-2062 | |
| 66 | Alex Thompson# | 45 | 2054-2061 | |
| 72 | Andrew Johnson | 44 | 2046-2057 | |
| 72 | José Martínez# | 44 | 2049-2063 | |
| 72 | Zhao-ji Qiu | 44 | 2036-2044 | |
| 72 | Sylvain Richard | 44 | 2042-2054 | |
| 76 | Truman Valentine | 43 | 2022-2031 | |
| 77 | Faisal bin Nabeel | 42 | 2034-2041 | |
| 77 | Ratko Davidovic | 42 | 2035-2043 | |
| 77 | Juan Díaz | 42 | 2025-2036 | |
| 77 | Vincent Hall | 42 | 2021-2031 | |
| 77 | Todd Hunter | 42 | 2047-2060 | |
| 77 | Ralph McKinney* | 42 | 2019-2034 | |
| 77 | Arnie Pittman | 42 | 2022-2030 | |
| 77 | Chase Sims | 42 | 2039-2049 | |
| 85 | Bailey Borrett | 41 | 2043-2052 | |
| 85 | Boris Milatovic | 41 | 2042-2057 | |
| 85 | Jorge Otero* | 41 | 2030-2040 | |
| 88 | Heath Brown | 40 | 2043-2053 | |
| 88 | Todd Johnson# | 40 | 2048-2060 | |
| 88 | Gilberto Malfeito# | 40 | 2057-2063 | |
| 88 | Kevin Nogilny* | 40 | 2032-2046 | |
| 88 | Joe Pruitt | 40 | 2031-2039 | |
| 88 | Armando Romano | 40 | 2029-2042 | |
| 88 | Juan Torres | 40 | 2021-2032 | |
| 95 | Craig Culver# | 39 | 2047-2061 | |
| 95 | Henry Hall | 39 | 2015-2026 | |
| 95 | Jeff McFarland# | 39 | 2048-2062 | |
| 95 | John Rigsby | 39 | 2034-2047 | |
| 95 | Luis Torres | 39 | 2024-2035 | |
| 95 | Brewster Warble | 39 | 2031-2046 |
