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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Lúcio Sánchez | 136 | 2017-2031 | |
| 2 | John Kaufman | 134 | 2017-2032 | |
| 3 | Jorge Aguirre | 132 | 2015-2032 | |
| 4 | Ramón Ortega | 131 | 2013-2028 | |
| 5 | Cris Mendoza | 123 | 2013-2029 | |
| 6 | Jim Eliott | 113 | 2014-2025 | |
| 7 | Alec Pittman | 111 | 2016-2030 | |
| 8 | Jesús Gonzáles# | 99 | 2019-2030 | |
| 9 | Ryan Davis | 98 | 2015-2026 | |
| 10 | Pedro Alejándrez# | 95 | 2021-2033 | |
| 10 | Manuel Rojas | 95 | 2018-2028 | |
| 12 | Ralph McKinney# | 94 | 2019-2033 | |
| 13 | Bill Oulton# | 93 | 2021-2033 | |
| 14 | Tom Reynolds | 92 | 2015-2028 | |
| 15 | Todd Hines | 91 | 2018-2032 | |
| 16 | Sozen Raikatuji | 87 | 2016-2023 | |
| 17 | Cordell Wilson | 83 | 2019-2030 | |
| 18 | Wes Hamm# | 77 | 2021-2033 | |
| 19 | Guillermo García | 76 | 2013-2021 | |
| 19 | Juan Júlio | 76 | 2013-2026 | |
| 21 | Kirby Brown | 75 | 2017-2029 | |
| 21 | José Hernández | 75 | 2013-2023 | |
| 23 | John Wilkins | 74 | 2013-2028 | |
| 24 | John Dempsey# | 72 | 2022-2033 | |
| 25 | Ryan Ray | 69 | 2013-2021 | |
| 25 | Josef van der Poel# | 69 | 2019-2033 | |
| 27 | Yoriyoshi Yamamoto | 67 | 2016-2026 | |
| 28 | Fraser Cuevas# | 63 | 2020-2032 | |
| 28 | Bruce Wright | 63 | 2020-2030 | |
| 30 | Wayne Craig | 62 | 2018-2030 | |
| 31 | Edwin Ellis | 61 | 2013-2019 | |
| 31 | Luis Flores# | 61 | 2024-2033 | |
| 31 | Chester Henry | 61 | 2016-2023 | |
| 34 | Jesús Franco# | 60 | 2026-2033 | |
| 34 | Yuri Volkers | 60 | 2013-2021 | |
| 36 | Jesús Caldero | 59 | 2018-2027 | |
| 36 | Vincent Hall | 59 | 2020-2032 | |
| 38 | Mimosa Joseph# | 58 | 2023-2033 | |
| 39 | Calvin Beck# | 56 | 2026-2033 | |
| 39 | Billy Crawford | 56 | 2014-2025 | |
| 39 | Aurelio López# | 56 | 2022-2033 | |
| 42 | Edgardo Marín | 55 | 2013-2032 | |
| 43 | John Coleman | 54 | 2013-2025 | |
| 43 | Ramón Molina# | 54 | 2026-2033 | |
| 45 | Iván García# | 53 | 2021-2033 | |
| 46 | Pablo De La Torre# | 50 | 2021-2033 | |
| 46 | José García# | 50 | 2022-2033 | |
| 48 | Natalino Golaio# | 49 | 2023-2033 | |
| 48 | Miguel Rubia# | 49 | 2029-2033 | |
| 50 | Ole Kos | 47 | 2018-2027 | |
| 51 | Raúl Areola# | 46 | 2020-2033 | |
| 51 | Wayne Hurst | 46 | 2015-2024 | |
| 53 | José Flores# | 45 | 2019-2029 | |
| 53 | Raúl Gómez# | 45 | 2027-2033 | |
| 53 | Kyle Lewis | 45 | 2016-2026 | |
| 56 | Vern Camp | 44 | 2013-2022 | |
| 56 | Yin-fat Foong | 44 | 2017-2029 | |
| 56 | Javier Ramírez | 44 | 2018-2027 | |
| 59 | Curtis Fields | 43 | 2016-2024 | |
| 60 | Pat Farrell | 42 | 2013-2022 | |
| 60 | Edgar Martínez | 42 | 2013-2021 | |
| 60 | Ilie Paunescu# | 42 | 2016-2033 | |
| 60 | Peter Rivers | 42 | 2013-2020 | |
| 64 | Allen Blair# | 41 | 2021-2033 | |
| 64 | Earnest Casey | 41 | 2018-2025 | |
| 64 | Bill Fletcher | 41 | 2018-2025 | |
| 67 | Charles Dobson# | 40 | 2024-2032 | |
| 67 | Devin Hinton | 40 | 2013-2023 | |
| 67 | Mario Peńa | 40 | 2013-2023 | |
| 70 | Gerardo Pagán# | 39 | 2027-2033 | |
| 71 | Tobías Pérez# | 38 | 2024-2033 | |
| 72 | Miguel Castillo | 37 | 2013-2020 | |
| 72 | Alejandro Guerra# | 37 | 2027-2033 | |
| 72 | Juan Torres# | 37 | 2023-2029 | |
| 75 | Erik Davis | 36 | 2013-2021 | |
| 75 | Eduardo Díaz | 36 | 2021-2028 | |
| 75 | Bill Grange | 36 | 2013-2017 | |
| 75 | Enrique Magana | 36 | 2013-2019 | |
| 75 | Addie Samson# | 36 | 2021-2033 | |
| 75 | Juan Valéncia# | 36 | 2023-2033 | |
| 81 | Burt Booth | 35 | 2013-2026 | |
| 81 | Kirby Buckner# | 35 | 2025-2030 | |
| 81 | Bartolomeu Lio# | 35 | 2018-2029 | |
| 81 | Pedro Ramírez# | 35 | 2023-2032 | |
| 81 | Germán Rodríguez# | 35 | 2024-2033 | |
| 81 | Jaime van de Weideven# | 35 | 2022-2033 | |
| 87 | Enrique Cortéz# | 34 | 2022-2032 | |
| 87 | Ken Hinkle | 34 | 2013-2026 | |
| 87 | Valentín Rivera# | 34 | 2026-2033 | |
| 90 | Reid Garner | 33 | 2015-2022 | |
| 90 | Eddie Kop# | 33 | 2025-2033 | |
| 90 | Tim Powell | 33 | 2013-2015 | |
| 93 | Adrián Fierro# | 32 | 2018-2033 | |
| 93 | Gene Kirkland | 32 | 2018-2032 | |
| 93 | Yoo-chul Mun# | 32 | 2031-2033 | |
| 93 | Pedro Ritodíaz | 32 | 2013-2024 | |
| 97 | Eugene Clarkston# | 31 | 2024-2033 | |
| 97 | George Frazier# | 31 | 2019-2033 | |
| 97 | Cole Hall | 31 | 2013-2027 | |
| 100 | Pedro Martínez | 30 | 2013-2017 |
