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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Shigemasa Horiuchi# | 105 | 2017-2029 | |
| 2 | Gary Bailey# | 82 | 2015-2029 | |
| 3 | Greg White# | 79 | 2015-2028 | |
| 4 | Carlos Sánchez# | 68 | 2021-2028 | |
| 5 | Sexto Rodríguez | 65 | 2015-2025 | |
| 6 | Benny York# | 63 | 2015-2029 | |
| 7 | Chip Bishop# | 62 | 2015-2029 | |
| 8 | Jon Briddon# | 56 | 2022-2029 | |
| 9 | José Alaniz# | 55 | 2016-2025 | |
| 9 | Lou Meadows# | 55 | 2016-2029 | |
| 11 | Gunner Hardy# | 52 | 2016-2028 | |
| 12 | Walt Coffman# | 48 | 2026-2029 | |
| 12 | Addie Samson# | 48 | 2024-2027 | |
| 14 | William MacKnight# | 47 | 2022-2028 | |
| 15 | Art Adams# | 45 | 2021-2029 | |
| 15 | John Brown# | 45 | 2017-2029 | |
| 17 | John Alvarado | 44 | 2017-2021 | |
| 17 | Tim Powell | 44 | 2015-2020 | |
| 19 | Melvin Haney# | 43 | 2023-2029 | |
| 20 | Roderick Rhodes# | 42 | 2015-2029 | |
| 21 | Cris Herrera# | 40 | 2024-2029 | |
| 22 | Woody Carlson# | 39 | 2020-2027 | |
| 22 | David Collingwood# | 39 | 2018-2028 | |
| 22 | Ronald Harmon# | 39 | 2016-2029 | |
| 22 | Matt Harris# | 39 | 2020-2029 | |
| 22 | Pedro Ritodíaz | 39 | 2015-2024 | |
| 27 | Félix Jiménez# | 38 | 2022-2026 | |
| 27 | Shunen Takahashi# | 38 | 2023-2029 | |
| 27 | Jeff Territt# | 38 | 2020-2029 | |
| 30 | Neil Gilliam# | 37 | 2021-2026 | |
| 30 | Eduardo Molina# | 37 | 2022-2025 | |
| 30 | Christian Patrick | 37 | 2019-2028 | |
| 30 | Alfonso Zapata# | 37 | 2022-2025 | |
| 34 | Doug Green# | 36 | 2022-2029 | |
| 34 | Kenshin Koike# | 36 | 2018-2027 | |
| 36 | Roberto Calderón# | 35 | 2026-2029 | |
| 36 | Jared Cox | 35 | 2016-2022 | |
| 36 | Leroy Moody# | 35 | 2025-2029 | |
| 36 | Jim Roberts | 35 | 2016-2020 | |
| 36 | Rusty Swanson# | 35 | 2026-2029 | |
| 36 | Hunter Wilson# | 35 | 2022-2027 | |
| 42 | Bob Compton | 34 | 2015-2023 | |
| 42 | Alfonso Miranda# | 34 | 2022-2029 | |
| 42 | Dan Mitchell# | 34 | 2020-2025 | |
| 42 | Bill Prowse | 34 | 2015-2020 | |
| 46 | Kent Clement# | 33 | 2021-2029 | |
| 46 | Harrison Jones | 33 | 2017-2021 | |
| 46 | Johnny Joyce | 33 | 2015-2019 | |
| 46 | Paul Lowery | 33 | 2015-2020 | |
| 46 | Lorenzo Sánchez# | 33 | 2020-2029 | |
| 51 | Jeff Bradshaw# | 32 | 2024-2029 | |
| 51 | Jorge Garza# | 32 | 2022-2027 | |
| 51 | Collin Hill# | 32 | 2020-2028 | |
| 51 | Clarence Ramsey | 32 | 2017-2022 | |
| 55 | Jorge Castillo# | 31 | 2020-2025 | |
| 55 | Yusuke Chikafuji# | 31 | 2024-2029 | |
| 55 | Roderick Draper | 31 | 2015-2021 | |
| 55 | Edison Larson# | 31 | 2020-2029 | |
| 55 | Luis Peña# | 31 | 2025-2029 | |
| 55 | Ryan Peterson# | 31 | 2026-2029 | |
| 61 | Mike Jones | 30 | 2016-2020 | |
| 61 | Jesús Tejeda# | 30 | 2023-2027 | |
| 63 | António Cruz | 29 | 2015-2020 | |
| 63 | Juan Montoya# | 29 | 2025-2029 | |
| 63 | Chuck Steele | 29 | 2018-2024 | |
| 66 | Esteban Costello | 28 | 2018-2021 | |
| 66 | Cisco Cruz | 28 | 2017-2025 | |
| 66 | Pat Farrell | 28 | 2015-2023 | |
| 66 | Roger Garrett | 28 | 2016-2024 | |
| 66 | Guillermo Pérez | 28 | 2017-2025 | |
| 71 | Kent Hubbard | 27 | 2015-2020 | |
| 71 | Javier Ramírez | 27 | 2018-2026 | |
| 71 | Bobby Swain# | 27 | 2024-2029 | |
| 71 | Sukejuro Yokoyama# | 27 | 2025-2027 | |
| 75 | Elvin Brooks# | 26 | 2017-2028 | |
| 75 | Jim Dixon | 26 | 2016-2027 | |
| 75 | George Frazier# | 26 | 2017-2028 | |
| 75 | Antonio Godfrey# | 26 | 2024-2028 | |
| 75 | Henry Hall# | 26 | 2017-2025 | |
| 75 | Todd Hines# | 26 | 2017-2026 | |
| 81 | Leslie Brooks# | 25 | 2021-2029 | |
| 81 | Cipriano Costa# | 25 | 2022-2026 | |
| 81 | Adrián Fierro# | 25 | 2020-2028 | |
| 81 | Bartolo González | 25 | 2015-2019 | |
| 81 | Jackson Haines# | 25 | 2016-2026 | |
| 81 | Rex Hood# | 25 | 2021-2025 | |
| 81 | Myron Johnson | 25 | 2015-2018 | |
| 81 | Tetsuzan Kaneko | 25 | 2018-2025 | |
| 81 | José Rico# | 25 | 2025-2028 | |
| 81 | Richard Sykes | 25 | 2017-2027 | |
| 81 | Dave Tomlinson | 25 | 2017-2026 | |
| 81 | Jimmy Whittier# | 25 | 2024-2026 | |
| 81 | Britt Yates | 25 | 2016-2023 | |
| 94 | Pedro Alejándrez# | 24 | 2020-2021 | |
| 94 | Jerry Clephane | 24 | 2015-2020 | |
| 94 | Luis Hernández# | 24 | 2025-2029 | |
| 94 | Randy Hoffman | 24 | 2017-2024 | |
| 94 | Marlon Miller | 24 | 2018-2026 | |
| 94 | Mathies Pilegaard | 24 | 2015-2025 | |
| 94 | José Reyna# | 24 | 2018-2022 |
