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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Silvio Bolt | 65 | 2026-2037 | |
| 1 | Félix Córdova | 65 | 2023-2035 | |
| 3 | José Silva# | 62 | 2027-2040 | |
| 4 | Jim Fish | 57 | 2024-2037 | |
| 4 | Kitahachi Noda# | 57 | 2024-2040 | |
| 6 | Robinson Hernández# | 52 | 2028-2038 | |
| 7 | Andrew Burns | 49 | 2021-2033 | |
| 7 | Shumei Suzuki# | 49 | 2037-2040 | |
| 9 | Alonso González# | 48 | 2034-2040 | |
| 9 | Kikaku Suzuki | 48 | 2022-2030 | |
| 11 | Leonardo González | 47 | 2014-2020 | |
| 12 | Todd Miller# | 46 | 2036-2040 | |
| 12 | Lúcio Saldaña# | 46 | 2035-2039 | |
| 14 | Joaquín Cerda# | 45 | 2028-2038 | |
| 14 | Izumo Kondo | 45 | 2025-2031 | |
| 16 | Neil Maes | 44 | 2016-2033 | |
| 17 | Dong-min Kim# | 43 | 2028-2034 | |
| 18 | Nobuhisa Nagai | 42 | 2017-2031 | |
| 19 | Marcos Alcorta | 41 | 2025-2030 | |
| 19 | Dan McClain | 41 | 2021-2024 | |
| 19 | Victor McKay | 41 | 2021-2037 | |
| 19 | Marcel Osterhout# | 41 | 2029-2040 | |
| 19 | Ricardo Salazar | 41 | 2011-2018 | |
| 19 | Seong-chae Somun# | 41 | 2029-2039 | |
| 25 | Kyoichi Gato | 40 | 2025-2028 | |
| 25 | Pedro Novaro# | 40 | 2027-2038 | |
| 25 | Rafael Quintero | 40 | 2019-2022 | |
| 28 | Matt Allison | 39 | 2019-2032 | |
| 28 | Donald Edwards | 39 | 2015-2023 | |
| 28 | Carlos Herrera# | 39 | 2037-2040 | |
| 28 | Ángel López# | 39 | 2030-2039 | |
| 28 | Roberto Rodríguez# | 39 | 2028-2039 | |
| 28 | Jesse Strickland | 39 | 2018-2021 | |
| 28 | Pedro Torres# | 39 | 2027-2040 | |
| 35 | José Aguilar | 38 | 2017-2029 | |
| 35 | Celestino Corisca# | 38 | 2028-2039 | |
| 35 | António García# | 38 | 2034-2040 | |
| 35 | Adam Pemberton# | 38 | 2027-2040 | |
| 35 | José Piña | 38 | 2007-2010 | |
| 35 | Frank Ridell# | 38 | 2030-2035 | |
| 41 | Jim Park | 37 | 2012-2017 | |
| 41 | Miguel Torres# | 37 | 2033-2038 | |
| 43 | Sebastiaan de Roode# | 36 | 2032-2033 | |
| 43 | Ángel Ramírez | 36 | 2021-2024 | |
| 43 | Norm Wood | 36 | 2024-2029 | |
| 46 | Jon Yates | 35 | 2020-2024 | |
| 47 | Elvis Carter | 34 | 2025-2029 | |
| 47 | Steve Casey | 34 | 2021-2035 | |
| 47 | Jake Conrad# | 34 | 2030-2037 | |
| 47 | José Estrada# | 34 | 2032-2039 | |
| 47 | Philip Klink | 34 | 2016-2024 | |
| 47 | Ronald Mitchell# | 34 | 2030-2039 | |
| 47 | Clarence Peterson | 34 | 2017-2030 | |
| 47 | Albert Thomas | 34 | 2007-2009 | |
| 47 | Paul Watts | 34 | 2032-2034 | |
| 56 | Thurman Collins | 33 | 2019-2021 | |
| 56 | Salvador Díaz | 33 | 2007-2015 | |
| 56 | Randy Hall | 33 | 2007-2014 | |
| 56 | Steve Struck# | 33 | 2027-2028 | |
| 56 | Barney Swanson# | 33 | 2027-2038 | |
| 61 | Bill Bowden | 32 | 2014-2023 | |
| 61 | Carlos Icaza | 32 | 2018-2021 | |
| 61 | Michael Ladner | 32 | 2017-2019 | |
| 61 | Min-zhong Lou# | 32 | 2034-2035 | |
| 61 | Jorge Luna | 32 | 2024-2037 | |
| 61 | Roy Mayes# | 32 | 2033-2038 | |
| 61 | Joe Parsons | 32 | 2009-2016 | |
| 61 | Juan Santana | 32 | 2022-2026 | |
| 61 | Barney Stone# | 32 | 2028-2038 | |
| 70 | Lou Butler# | 31 | 2029-2040 | |
| 70 | Juan Colón# | 31 | 2036-2040 | |
| 70 | Luis González# | 31 | 2035-2040 | |
| 70 | Rich Herrera# | 31 | 2037-2040 | |
| 70 | Jaime Melenas | 31 | 2011-2013 | |
| 70 | Jerry Pearson | 31 | 2028-2033 | |
| 70 | Dylan Stinson# | 31 | 2034-2039 | |
| 77 | Fred Arrington | 30 | 2007-2014 | |
| 77 | Lloyd Caylor | 30 | 2011-2019 | |
| 77 | Adrián Cortéz | 30 | 2014-2018 | |
| 77 | Hou Hao | 30 | 2021-2033 | |
| 77 | Tsurayuki Harada# | 30 | 2029-2040 | |
| 77 | Landon Hart | 30 | 2015-2022 | |
| 77 | Marvin Lilly | 30 | 2020-2025 | |
| 77 | Bill Martin | 30 | 2019-2032 | |
| 77 | Ernesto Pérez# | 30 | 2037-2038 | |
| 77 | José Pérez | 30 | 2007-2015 | |
| 77 | Héctor Rivera | 30 | 2021-2038 | |
| 88 | Ángelo Castro | 29 | 2015-2022 | |
| 88 | Pablo Flores# | 29 | 2032-2036 | |
| 88 | Skip Hathaway# | 29 | 2033-2036 | |
| 88 | Sotatsu Hirano | 29 | 2022-2028 | |
| 88 | Lance Kinney | 29 | 2024-2031 | |
| 88 | Eric Massey | 29 | 2020-2023 | |
| 88 | Armando Pérez | 29 | 2007-2013 | |
| 88 | Edgar Rojas | 29 | 2009-2012 | |
| 88 | Barney Stevens | 29 | 2027-2035 | |
| 97 | Brock Barrett | 28 | 2012-2025 | |
| 97 | Bart Belcham | 28 | 2024-2034 | |
| 97 | George Brown# | 28 | 2036-2040 | |
| 97 | Reid Daniel | 28 | 2024-2027 |
