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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Nathan Seymour | 94 | 2020-2026 | |
| 2 | Santiago González | 82 | 2017-2026 | |
| 3 | Gildun Ouakili | 73 | 2011-2021 | |
| 4 | Gilberto Barrera | 69 | 2013-2019 | |
| 4 | Luis Franco | 69 | 2008-2015 | |
| 6 | John Martin | 59 | 2009-2015 | |
| 6 | Armando Rodríguez | 59 | 2024-2028 | |
| 8 | Román Zamora# | 56 | 2033-2038 | |
| 9 | Juan Aguilar | 53 | 2017-2023 | |
| 10 | Javier Santos# | 51 | 2031-2037 | |
| 11 | Esteban Aragón# | 50 | 2034-2038 | |
| 12 | Hokusai Nakashima | 49 | 2015-2019 | |
| 12 | José Zamora# | 49 | 2031-2037 | |
| 14 | Mario Solíz | 47 | 2013-2024 | |
| 15 | Javier González | 44 | 2024-2027 | |
| 16 | Irving Baker | 43 | 2012-2015 | |
| 16 | Emerson Gibbon# | 43 | 2034-2038 | |
| 16 | John McGuire# | 43 | 2033-2038 | |
| 19 | Davey Huckaby | 42 | 2010-2016 | |
| 19 | Kent Smith | 42 | 2028-2031 | |
| 21 | Alejandro Guzmán# | 41 | 2024-2033 | |
| 21 | Ramón López | 41 | 2013-2017 | |
| 21 | Don Wiggins | 41 | 2024-2029 | |
| 24 | Gerald Collins# | 40 | 2032-2036 | |
| 24 | Cordell Hensley | 40 | 2011-2019 | |
| 26 | Mark Anderson | 39 | 2024-2026 | |
| 26 | Beau Montgomery | 39 | 2024-2029 | |
| 28 | Juan Díaz# | 38 | 2029-2034 | |
| 28 | José Meléndez# | 38 | 2032-2038 | |
| 30 | Steve Harris# | 37 | 2030-2036 | |
| 30 | Luis Valentín | 37 | 2014-2017 | |
| 30 | Ed Weaver# | 37 | 2031-2033 | |
| 33 | Nick Clayton | 36 | 2027-2032 | |
| 33 | Chad Field | 36 | 2020-2023 | |
| 33 | Leonard Fitzpatrick# | 36 | 2032-2037 | |
| 33 | Ramón Quintero | 36 | 2024-2026 | |
| 37 | John Kelly | 35 | 2027-2033 | |
| 37 | José Reyes# | 35 | 2031-2037 | |
| 39 | Esteban Gonzáles | 34 | 2017-2020 | |
| 39 | Dan Jones# | 34 | 2029-2033 | |
| 39 | Mario Peńa | 34 | 2011-2013 | |
| 39 | Jorge Ruíz | 34 | 2021-2023 | |
| 39 | Neil Snow | 34 | 2026-2030 | |
| 39 | John Stephenson# | 34 | 2033-2038 | |
| 39 | Cipriano Vega# | 34 | 2032-2038 | |
| 46 | Lou Ferrell# | 33 | 2035-2038 | |
| 46 | Akihisa Nishimura | 33 | 2017-2023 | |
| 46 | Walt Thompson | 33 | 2010-2015 | |
| 46 | Josh Young | 33 | 2027-2030 | |
| 50 | Bobby Burnett# | 32 | 2036-2038 | |
| 50 | Armand Calazzo | 32 | 2021-2023 | |
| 50 | Ramón Cruz | 32 | 2010-2011 | |
| 50 | Alfonso Garza# | 32 | 2032-2036 | |
| 50 | Shiki Kanno | 32 | 2016-2018 | |
| 50 | Alex Stanford# | 32 | 2023-2027 | |
| 50 | Mike Waddingham# | 32 | 2036-2038 | |
| 50 | Jim Wither# | 32 | 2034-2036 | |
| 58 | Nick Davis# | 31 | 2033-2038 | |
| 58 | Sandro Gonzáles | 31 | 2014-2017 | |
| 58 | Claudio Martínez# | 31 | 2022-2024 | |
| 58 | Pedro Mendoza | 31 | 2025-2026 | |
| 58 | Emílio Merced# | 31 | 2034-2038 | |
| 58 | Davis Morgan# | 31 | 2034-2036 | |
| 58 | Pierre-Olivier Morin | 31 | 2031-2034 | |
| 65 | Juan Juárez# | 30 | 2030-2036 | |
| 65 | Francisco Rodríguez# | 30 | 2026-2030 | |
| 65 | Brody Sellers# | 30 | 2034-2037 | |
| 68 | Armando Avilés | 29 | 2020-2022 | |
| 69 | Erwin Entwistle | 28 | 2025-2026 | |
| 69 | Sergio García | 28 | 2011-2014 | |
| 69 | Tom Land# | 28 | 2032-2034 | |
| 69 | António Rodríguez# | 28 | 2029-2033 | |
| 69 | Mang Tow | 28 | 2013-2016 | |
| 74 | Lorenzo Aguilar# | 27 | 2023-2025 | |
| 74 | Robbie Daniel | 27 | 2019-2022 | |
| 74 | Manuel Encarnación# | 27 | 2027-2032 | |
| 74 | Ángel Fernández# | 27 | 2033-2035 | |
| 74 | Héctor Ortíz# | 27 | 2032-2038 | |
| 74 | Júlio Pérez# | 27 | 2035-2037 | |
| 74 | Rubén Rico | 27 | 2021-2026 | |
| 74 | Albert Sánchez# | 27 | 2028-2031 | |
| 82 | Myron Garrett | 26 | 2013-2016 | |
| 82 | Gary Grimes | 26 | 2024-2026 | |
| 82 | Manuel Guel# | 26 | 2029-2034 | |
| 82 | Robby Hall | 26 | 2019-2026 | |
| 82 | Thomas Heath | 26 | 2015-2017 | |
| 82 | James Jones# | 26 | 2033-2037 | |
| 82 | Clarence Skerratt | 26 | 2022-2025 | |
| 82 | Tim Sullivan | 26 | 2010-2012 | |
| 82 | Raúl Vélez# | 26 | 2033-2037 | |
| 82 | Albert Wallace | 26 | 2011-2017 | |
| 82 | Wilson Yoxall | 26 | 2027-2030 | |
| 93 | Bob Coture | 25 | 2010-2020 | |
| 93 | Bryce Davis | 25 | 2025-2029 | |
| 93 | António Gálvez | 25 | 2012-2014 | |
| 93 | Will Huggins | 25 | 2013-2020 | |
| 93 | Chris King | 25 | 2012-2017 | |
| 93 | Rodrigo Matos# | 25 | 2034-2038 | |
| 93 | Ramón Méndez | 25 | 2010-2020 | |
| 93 | Rob Price | 25 | 2026-2028 |
