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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 | Eddie Kop# | 74 | 2023-2041 | |
| 8 | Pedro Valdéz | 68 | 2020-2040 | |
| 9 | Robbie Baxter | 64 | 2022-2037 | |
| 10 | Javier Mora | 63 | 2020-2034 | |
| 11 | Walt Coffman | 61 | 2026-2038 | |
| 12 | Wes Hamm | 60 | 2021-2037 | |
| 13 | Héctor Alarcon | 57 | 2015-2027 | |
| 13 | Paul Díaz | 57 | 2019-2030 | |
| 15 | Wayne Craig | 56 | 2015-2023 | |
| 16 | Allen Yohemas | 55 | 2022-2031 | |
| 17 | Andy Coker | 54 | 2016-2026 | |
| 17 | Wayne Hurst | 54 | 2015-2028 | |
| 19 | David Moore# | 53 | 2034-2041 | |
| 19 | Domingo Ramírez | 53 | 2022-2039 | |
| 19 | Jesús Vidro# | 53 | 2033-2038 | |
| 22 | Pedro Castro | 49 | 2018-2032 | |
| 22 | Stanford McCain# | 49 | 2031-2041 | |
| 22 | Gustavo Tobías# | 49 | 2032-2041 | |
| 25 | Chip Bishop | 48 | 2018-2028 | |
| 25 | Allen Blair | 48 | 2015-2032 | |
| 25 | Tyler MacHugh | 48 | 2023-2033 | |
| 25 | Bobby Swain | 48 | 2020-2031 | |
| 25 | John Wilkins* | 48 | 2015-2026 | |
| 25 | Stanley Yelnats | 48 | 2030-2038 | |
| 31 | John Braun | 46 | 2014-2022 | |
| 31 | John Holley | 46 | 2014-2022 | |
| 31 | Roderick Rhodes | 46 | 2017-2028 | |
| 34 | Anatoly Ivanovich | 45 | 2030-2039 | |
| 34 | Aurelio López | 45 | 2022-2037 | |
| 36 | Matthew Fallows# | 43 | 2034-2041 | |
| 36 | Truman Valentine | 43 | 2022-2031 | |
| 38 | Faisal bin Nabeel# | 42 | 2034-2041 | |
| 38 | Juan Díaz | 42 | 2025-2036 | |
| 38 | Vincent Hall | 42 | 2021-2031 | |
| 38 | Ralph McKinney* | 42 | 2019-2034 | |
| 38 | Arnie Pittman | 42 | 2022-2030 | |
| 43 | Jorge Otero | 41 | 2030-2040 | |
| 44 | Kevin Nogilny# | 40 | 2032-2040 | |
| 44 | Joe Pruitt# | 40 | 2031-2039 | |
| 44 | Zhao-ji Qiu# | 40 | 2036-2041 | |
| 44 | Juan Torres | 40 | 2021-2032 | |
| 48 | Henry Hall | 39 | 2015-2026 | |
| 48 | Armando Romano# | 39 | 2029-2041 | |
| 48 | Luis Torres | 39 | 2024-2035 | |
| 51 | Michael Battle | 38 | 2017-2021 | |
| 51 | George Frazier | 38 | 2017-2036 | |
| 51 | Ton Jobse# | 38 | 2031-2037 | |
| 51 | Lynwood Matos | 38 | 2021-2031 | |
| 51 | Guillermo Pérez | 38 | 2015-2025 | |
| 56 | Pat Horton | 37 | 2014-2019 | |
| 56 | Cory Sanders | 37 | 2021-2036 | |
| 56 | Brantford Winstworth III# | 37 | 2029-2041 | |
| 59 | António Marés | 36 | 2024-2031 | |
| 59 | António Muñóz | 36 | 2029-2039 | |
| 61 | Manuel Delgadillo | 35 | 2028-2038 | |
| 61 | Ricardo Hernández | 35 | 2014-2018 | |
| 61 | Chris Holland# | 35 | 2035-2040 | |
| 61 | Félix Jiménez | 35 | 2018-2028 | |
| 61 | Raúl Luna | 35 | 2028-2036 | |
| 61 | Rafael Rodríguez | 35 | 2026-2031 | |
| 61 | Hunter Wilson | 35 | 2019-2031 | |
| 61 | Benny York | 35 | 2016-2027 | |
| 69 | Gavin Blackburn | 34 | 2017-2032 | |
| 69 | Pablo De La Torre | 34 | 2022-2036 | |
| 69 | Maru Pao Pao# | 34 | 2029-2037 | |
| 69 | Rafael Rivera | 34 | 2027-2039 | |
| 69 | Germán Rodríguez | 34 | 2025-2040 | |
| 69 | Brandeis Vogt | 34 | 2022-2036 | |
| 75 | Gary Bailey | 33 | 2022-2031 | |
| 75 | Jon Dunn | 33 | 2024-2034 | |
| 75 | Roger Garrett | 33 | 2014-2024 | |
| 75 | Lou Hartling | 33 | 2019-2030 | |
| 75 | Nelle Liefting | 33 | 2022-2036 | |
| 75 | Michael Machen# | 33 | 2029-2041 | |
| 75 | Keisuke Nishida | 33 | 2027-2032 | |
| 75 | Francisco Valdés | 33 | 2022-2033 | |
| 83 | Manny Caraballo | 32 | 2022-2028 | |
| 83 | Zaki Fakhiri# | 32 | 2034-2040 | |
| 83 | Ji Jing | 32 | 2027-2035 | |
| 83 | Drake Montgomery | 32 | 2015-2020 | |
| 83 | Roger Rodenburg# | 32 | 2036-2041 | |
| 83 | Javier Roldán | 32 | 2025-2032 | |
| 83 | Decheng Sun | 32 | 2018-2028 | |
| 90 | Anastasio Cabanillas Jr.# | 31 | 2037-2041 | |
| 90 | Adrián Fierro | 31 | 2017-2032 | |
| 90 | Kyuichi Hori# | 31 | 2031-2041 | |
| 90 | Rich Hunter | 31 | 2014-2021 | |
| 90 | Rusty Swanson | 31 | 2025-2037 | |
| 90 | Aaron Wise | 31 | 2019-2029 | |
| 96 | Leslie Brooks | 30 | 2019-2030 | |
| 96 | António Castillo | 30 | 2026-2037 | |
| 96 | Ralph DePalma# | 30 | 2036-2041 | |
| 96 | Carlos Medina | 30 | 2029-2035 | |
| 100 | Art Adams | 29 | 2020-2031 |
