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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jeff Payton | 52 | 2022-2024 | |
| 2 | Michael Gladden | 45 | 2015-2018 | |
| 3 | Bill Moore# | 42 | 2044-2047 | |
| 4 | Tony McCain | 41 | 2019-2021 | |
| 5 | Harold Ingram | 37 | 2032-2047 | |
| 6 | Pedro Moreno | 36 | 2021-2023 | |
| 7 | Pedro Fernández | 35 | 2021-2023 | |
| 8 | William Lutz# | 34 | 2045-2048 | |
| 9 | Héctor Hernández# | 33 | 2045-2047 | |
| 10 | Charles Díaz | 32 | 2034-2037 | |
| 10 | Brian Escobar | 32 | 2028-2031 | |
| 10 | Felipe García# | 32 | 2047-2050 | |
| 13 | Allen Price | 31 | 2033-2035 | |
| 14 | Jimmy Miller | 30 | 2029-2030 | |
| 14 | Alberto Molina | 30 | 2014-2017 | |
| 16 | Kenny Ford# | 29 | 2047-2051 | |
| 16 | Clyde Williams | 29 | 2029-2031 | |
| 18 | Júlio Bruno | 28 | 2015-2017 | |
| 18 | Flint Hardy# | 28 | 2040-2043 | |
| 18 | Wesley Parlo# | 28 | 2034-2035 | |
| 21 | Martin Murphy | 27 | 2021-2023 | |
| 22 | Sozui Daikawa# | 26 | 2039-2042 | |
| 22 | Roosevelt Hill | 26 | 2034-2036 | |
| 24 | Joe Fish | 25 | 2028-2030 | |
| 24 | René Girard# | 25 | 2046-2047 | |
| 24 | José Rodríguez# | 25 | 2039-2040 | |
| 24 | Tom Shafer# | 25 | 2038-2040 | |
| 24 | Harold Sutton# | 25 | 2041-2044 | |
| 24 | William Young | 25 | 2018-2031 | |
| 30 | Connor Clay# | 24 | 2048-2050 | |
| 30 | Jimmy Young# | 24 | 2049-2051 | |
| 32 | John Ausenhus | 23 | 2033-2035 | |
| 32 | Pepe Ávila | 23 | 2024-2033 | |
| 32 | Bryan Lewis | 23 | 2036-2038 | |
| 32 | Javier Lópes# | 23 | 2048-2049 | |
| 32 | Pedro Reyes | 23 | 2041-2042 | |
| 32 | David Rivera | 23 | 2022-2024 | |
| 38 | Ben Craig | 22 | 2019-2020 | |
| 38 | Chris Crawford# | 22 | 2047-2049 | |
| 38 | James Crouch | 22 | 2017-2019 | |
| 38 | Julián Fernández | 22 | 2034-2036 | |
| 38 | Ángelo López# | 22 | 2039-2041 | |
| 38 | Marvin Margaret | 22 | 2013-2015 | |
| 38 | Keith Martin# | 22 | 2040-2041 | |
| 38 | Luis Pérez | 22 | 2019-2020 | |
| 38 | Paco Ramírez# | 22 | 2046-2048 | |
| 38 | Gustavo Reyes# | 22 | 2045-2048 | |
| 38 | Jonathan Sellek# | 22 | 2044-2045 | |
| 49 | Tex Baldwin# | 21 | 2045-2046 | |
| 49 | Francisco Fuentes# | 21 | 2045-2046 | |
| 49 | Pablo Gutiérrez | 21 | 2035-2036 | |
| 49 | Joe Hunt | 21 | 2023-2024 | |
| 49 | Carlos López# | 21 | 2039-2041 | |
| 49 | Geoffrey Lowe# | 21 | 2047-2049 | |
| 49 | Duane Pérez | 21 | 2031-2033 | |
| 49 | Étienne Roy | 21 | 2013-2015 | |
| 57 | Will Adams | 20 | 2014-2016 | |
| 57 | Orlando Caraballo# | 20 | 2048-2049 | |
| 57 | Robinson Castro | 20 | 2036-2038 | |
| 57 | Greg Goodenough# | 20 | 2046-2048 | |
| 57 | Arthur Humphrey | 20 | 2030-2048 | |
| 57 | Carl Jenkins# | 20 | 2034-2036 | |
| 57 | Robbie Lamb# | 20 | 2046-2047 | |
| 57 | Will Lester | 20 | 2019-2020 | |
| 57 | Jim Miller | 20 | 2027-2028 | |
| 57 | Jim Quick# | 20 | 2044-2046 | |
| 57 | Kenny Ruffin | 20 | 2025-2026 | |
| 57 | Toby Valentín# | 20 | 2046-2047 | |
| 57 | Gerardo Zúñiga | 20 | 2022-2024 | |
| 70 | John Cain# | 19 | 2042-2044 | |
| 70 | Todd Daniels | 19 | 2026-2027 | |
| 70 | Ramón Domínguez# | 19 | 2045-2046 | |
| 70 | Tim Hargrove# | 19 | 2045-2047 | |
| 70 | Keith Johnson | 19 | 2018-2020 | |
| 70 | Mario Mercado# | 19 | 2045-2048 | |
| 70 | Hoshi Nakamura | 19 | 2034-2035 | |
| 70 | Luis Olivares# | 19 | 2045-2046 | |
| 70 | Clay Patterson | 19 | 2034-2036 | |
| 70 | Sam Richards# | 19 | 2043-2044 | |
| 70 | Reynaldo Rosário# | 19 | 2043-2044 | |
| 70 | Mike Smith | 19 | 2015-2017 | |
| 70 | Artie Wade# | 19 | 2046-2048 | |
| 70 | Scott Wilkins | 19 | 2025-2027 | |
| 70 | Hugh Zhang# | 19 | 2046-2049 | |
| 85 | Lucas Barreiras | 18 | 2024-2040 | |
| 85 | Jeff Boyd# | 18 | 2046-2047 | |
| 85 | Joe Davidson | 18 | 2028-2029 | |
| 85 | Steve Hewitt | 18 | 2024-2024 | |
| 85 | Nolan Leeson# | 18 | 2044-2046 | |
| 85 | Dave MacDonald | 18 | 2036-2038 | |
| 85 | Jake Martin | 18 | 2038-2045 | |
| 85 | Peter Olson | 18 | 2017-2019 | |
| 85 | Aaron Peterson# | 18 | 2040-2046 | |
| 85 | Robert Ramsey | 18 | 2047-2047 | |
| 85 | Alejandro Sáenz | 18 | 2038-2039 | |
| 85 | Luis Antonio Silva# | 18 | 2046-2049 | |
| 85 | Dontrelle Willis# | 18 | 2049-2050 | |
| 98 | Iván Bernard | 17 | 2016-2019 | |
| 98 | Eric Bruce | 17 | 2012-2014 | |
| 98 | Juan Cardona# | 17 | 2042-2044 |
