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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Bill Critch | 89 | 2019-2031 | |
| 2 | Carlos Rivera# | 86 | 2025-2035 | |
| 3 | John Hoffman | 84 | 2014-2026 | |
| 4 | Felipe Martínez | 80 | 2025-2033 | |
| 5 | Alfredo Herrero | 79 | 2013-2021 | |
| 6 | John Haase | 75 | 2013-2027 | |
| 7 | Thomas Moore | 74 | 2013-2024 | |
| 8 | Balta Riojas | 73 | 2015-2023 | |
| 9 | Jeff William# | 72 | 2027-2035 | |
| 10 | Claudio Sánchez | 71 | 2021-2032 | |
| 11 | Floyd Crown | 68 | 2016-2029 | |
| 12 | Samuel Rodledo# | 66 | 2024-2035 | |
| 13 | Rogelio Castro | 64 | 2013-2026 | |
| 13 | Antonio Cuellar | 64 | 2015-2024 | |
| 15 | Earl Brown | 62 | 2014-2021 | |
| 15 | Coy Hendon | 62 | 2015-2022 | |
| 15 | Shawn MacNeill | 62 | 2024-2033 | |
| 18 | Gordon Gaddy | 60 | 2016-2026 | |
| 18 | William Haner | 60 | 2016-2022 | |
| 18 | Brian Thomas | 60 | 2016-2024 | |
| 21 | Armando Feliciano# | 59 | 2026-2035 | |
| 21 | Brian Harrington# | 59 | 2026-2034 | |
| 21 | Mark Tyler | 59 | 2022-2027 | |
| 24 | David Reimers | 58 | 2013-2021 | |
| 25 | Edgardo Barbosa | 57 | 2022-2032 | |
| 25 | Peter Payton# | 57 | 2024-2032 | |
| 27 | Roland Bucholtz# | 56 | 2030-2035 | |
| 27 | David Clark | 56 | 2019-2026 | |
| 29 | Hun-ho Pang# | 55 | 2026-2035 | |
| 30 | Kevin Gordon# | 54 | 2026-2035 | |
| 30 | Noah Hill | 54 | 2022-2034 | |
| 30 | Pancho López | 54 | 2017-2023 | |
| 30 | Thomas Marcell | 54 | 2014-2023 | |
| 30 | Will Walker | 54 | 2025-2033 | |
| 35 | Fred Jones | 53 | 2013-2020 | |
| 35 | Carl Shepherd | 53 | 2013-2018 | |
| 35 | Tony Zavala | 53 | 2014-2023 | |
| 38 | Larry Gabrielson | 52 | 2013-2020 | |
| 38 | Marc Powell | 52 | 2013-2024 | |
| 38 | Michael Sanders | 52 | 2013-2025 | |
| 41 | Bill Mobley | 51 | 2023-2032 | |
| 41 | Clayton Robison | 51 | 2020-2029 | |
| 41 | Lou Shaw | 51 | 2023-2035 | |
| 44 | Jeff Baldwin# | 50 | 2023-2035 | |
| 44 | Jose Lamela | 50 | 2014-2023 | |
| 44 | Carlos Morales# | 50 | 2026-2034 | |
| 44 | Willian Stewart | 50 | 2013-2023 | |
| 44 | Agustin Vasco | 50 | 2014-2021 | |
| 49 | Alan Blessing | 49 | 2015-2023 | |
| 49 | Juan Guzman | 49 | 2017-2027 | |
| 49 | Tsurugorou Shunko | 49 | 2013-2022 | |
| 49 | Bartho Witter | 49 | 2026-2031 | |
| 53 | Pete Boyle# | 48 | 2027-2035 | |
| 53 | Jesús Cruz | 48 | 2026-2033 | |
| 53 | Jesse Decaro | 48 | 2014-2018 | |
| 53 | Austin Houston# | 48 | 2030-2034 | |
| 53 | Gil Moore | 48 | 2021-2028 | |
| 58 | Gastone Capasso# | 47 | 2032-2035 | |
| 58 | Folkert Parrel | 47 | 2022-2033 | |
| 60 | Lawrence Heiner | 46 | 2014-2028 | |
| 60 | Jorge Menéndez# | 46 | 2028-2035 | |
| 60 | Michael Montgomery | 46 | 2015-2025 | |
| 60 | António Salinas# | 46 | 2022-2031 | |
| 64 | Matthew Cassity | 45 | 2013-2016 | |
| 64 | Woodrow Claytor | 45 | 2014-2021 | |
| 64 | Claudio Flores# | 45 | 2023-2035 | |
| 64 | Alfredo Hernández | 45 | 2026-2033 | |
| 64 | Luis Martínez# | 45 | 2027-2035 | |
| 64 | Shawn Schneider | 45 | 2027-2031 | |
| 64 | Aaron Taub | 45 | 2013-2017 | |
| 71 | Ron Grimes# | 44 | 2029-2035 | |
| 71 | Brain Thorn | 44 | 2013-2018 | |
| 71 | Bill Tidwell | 44 | 2028-2033 | |
| 71 | James Vidrio | 44 | 2019-2023 | |
| 75 | Takeo Hagi# | 43 | 2026-2035 | |
| 76 | Jermaine Earp | 42 | 2013-2022 | |
| 76 | Charles Olaughlin | 42 | 2013-2018 | |
| 76 | Bartolo Olivarez | 42 | 2018-2030 | |
| 76 | Tuan Olmstead | 42 | 2013-2019 | |
| 76 | Ichizo Sakamoto | 42 | 2021-2027 | |
| 76 | José Salazar# | 42 | 2027-2035 | |
| 82 | Buster Ducharme | 41 | 2013-2021 | |
| 82 | Einar Gaona | 41 | 2013-2016 | |
| 82 | David Rutledge | 41 | 2013-2020 | |
| 82 | Justin Thompson# | 41 | 2027-2034 | |
| 86 | Alonso Chlula | 40 | 2020-2033 | |
| 86 | Daniel Gibson | 40 | 2021-2026 | |
| 86 | Raúl Orosco | 40 | 2025-2032 | |
| 86 | Rafael Rojas# | 40 | 2021-2035 | |
| 86 | Lewis Trapp | 40 | 2017-2026 | |
| 86 | Pat Young | 40 | 2022-2026 | |
| 92 | William Connolly | 39 | 2013-2019 | |
| 92 | Clarence Craig | 39 | 2014-2028 | |
| 92 | Isidro Frau | 39 | 2016-2022 | |
| 92 | Carlos Salazar# | 39 | 2030-2035 | |
| 92 | Darryl Sears | 39 | 2023-2030 | |
| 92 | David Vaccaro | 39 | 2013-2025 | |
| 98 | Jerry Brennan# | 38 | 2030-2035 | |
| 98 | Salomon Candelas | 38 | 2014-2024 | |
| 98 | Marvin Chavarria | 38 | 2016-2020 |
