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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Nathaniel Riley | 12 | 2016-2030 | |
| 2 | Bobby Swain | 11 | 2020-2031 | |
| 3 | Pedro Castro | 10 | 2018-2032 | |
| 3 | Wes Hamm* | 10 | 2021-2037 | |
| 3 | Eddie Kop | 10 | 2023-2042 | |
| 3 | Gustavo Tobías | 10 | 2032-2044 | |
| 7 | Andy Coker | 9 | 2016-2026 | |
| 7 | Wayne Craig | 9 | 2015-2023 | |
| 7 | Allen Yohemas | 9 | 2022-2031 | |
| 10 | Chip Bishop | 8 | 2018-2028 | |
| 10 | Vincent Hall | 8 | 2021-2031 | |
| 10 | Javier Mora | 8 | 2020-2034 | |
| 10 | Juan Torres | 8 | 2021-2032 | |
| 14 | Rafael Cardona | 7 | 2022-2035 | |
| 14 | Matthew Fallows# | 7 | 2034-2046 | |
| 14 | Cris Mendoza | 7 | 2017-2029 | |
| 14 | Kevin Nogilny# | 7 | 2032-2046 | |
| 14 | Jorge Otero | 7 | 2030-2040 | |
| 14 | Elroy Thompkins | 7 | 2029-2043 | |
| 14 | Bill Tugwell | 7 | 2029-2034 | |
| 21 | Robbie Baxter | 6 | 2022-2037 | |
| 21 | Dave Becker# | 6 | 2040-2046 | |
| 21 | Kent Clement | 6 | 2022-2033 | |
| 21 | David Collingwood | 6 | 2019-2028 | |
| 21 | John Dempsey | 6 | 2022-2036 | |
| 21 | Juan Díaz | 6 | 2025-2036 | |
| 21 | Zaki Fakhiri# | 6 | 2034-2046 | |
| 21 | George Frazier | 6 | 2017-2036 | |
| 21 | Juan Guillén* | 6 | 2027-2039 | |
| 21 | Cole Hall | 6 | 2016-2027 | |
| 21 | John Holley | 6 | 2014-2022 | |
| 21 | Tsugahara Hori | 6 | 2029-2040 | |
| 21 | Anatoly Ivanovich | 6 | 2030-2039 | |
| 21 | Bartolomeu Lio | 6 | 2019-2034 | |
| 21 | Jeff Mahl | 6 | 2035-2046 | |
| 21 | Lou Meadows | 6 | 2016-2027 | |
| 21 | José Quiñones | 6 | 2034-2043 | |
| 21 | Roderick Rhodes | 6 | 2017-2028 | |
| 21 | Cory Sanders | 6 | 2021-2036 | |
| 21 | Quintiliano Seixal | 6 | 2025-2037 | |
| 21 | Chase Sims# | 6 | 2039-2045 | |
| 21 | Pedro Valdéz | 6 | 2020-2040 | |
| 21 | Jesús Vidro# | 6 | 2033-2045 | |
| 44 | Gary Bailey* | 5 | 2022-2031 | |
| 44 | John Brown | 5 | 2016-2031 | |
| 44 | Juan Contreras | 5 | 2030-2042 | |
| 44 | Dorian Daly | 5 | 2028-2036 | |
| 44 | Pablo De La Torre | 5 | 2022-2036 | |
| 44 | Manuel Delgadillo | 5 | 2028-2038 | |
| 44 | Paul Díaz | 5 | 2019-2030 | |
| 44 | Craig Fitzgerald# | 5 | 2036-2046 | |
| 44 | Stewart Fleming | 5 | 2029-2033 | |
| 44 | Jesús Franco | 5 | 2028-2034 | |
| 44 | Raúl Gómez | 5 | 2026-2034 | |
| 44 | Henry Hall | 5 | 2015-2026 | |
| 44 | Van Hileman# | 5 | 2041-2046 | |
| 44 | Hong-bin Hua# | 5 | 2037-2046 | |
| 44 | Wayne Hurst | 5 | 2015-2028 | |
| 44 | Masami Kogawa | 5 | 2031-2034 | |
| 44 | Edison Larson | 5 | 2020-2038 | |
| 44 | Raúl Luna | 5 | 2028-2036 | |
| 44 | Michael Machen | 5 | 2029-2041 | |
| 44 | Eric Matson | 5 | 2027-2041 | |
| 44 | Francis McBride | 5 | 2023-2027 | |
| 44 | Gerardo Pagán | 5 | 2027-2036 | |
| 44 | Milutin Panic# | 5 | 2040-2046 | |
| 44 | Maru Pao Pao | 5 | 2029-2037 | |
| 44 | Joe Pruitt | 5 | 2031-2039 | |
| 44 | Domingo Ramírez | 5 | 2022-2039 | |
| 44 | Lorenzo Sánchez | 5 | 2020-2033 | |
| 44 | Stanley Yelnats | 5 | 2030-2038 | |
| 72 | Art Adams | 4 | 2020-2031 | |
| 72 | José Alaniz | 4 | 2020-2030 | |
| 72 | Javier Ariza# | 4 | 2040-2045 | |
| 72 | Gary Ashley# | 4 | 2034-2044 | |
| 72 | Luqman Barcoo | 4 | 2032-2035 | |
| 72 | Hermenegildo Beliago | 4 | 2027-2043 | |
| 72 | Faisal bin Nabeel | 4 | 2034-2041 | |
| 72 | Allen Blair | 4 | 2015-2032 | |
| 72 | Kyle Boddy | 4 | 2026-2034 | |
| 72 | Sjaak Bonne | 4 | 2027-2041 | |
| 72 | Quentin Bowers | 4 | 2028-2038 | |
| 72 | John Braun | 4 | 2014-2022 | |
| 72 | Alfonso Caballero# | 4 | 2038-2045 | |
| 72 | José Cotilla | 4 | 2032-2041 | |
| 72 | Billy Crawford | 4 | 2017-2025 | |
| 72 | Joe Crown | 4 | 2015-2026 | |
| 72 | Jesús Cruz# | 4 | 2038-2045 | |
| 72 | Kenete Daku | 4 | 2029-2039 | |
| 72 | Paul Dudding | 4 | 2033-2038 | |
| 72 | Urs Ehles# | 4 | 2036-2045 | |
| 72 | Lorenzo Fabián | 4 | 2029-2041 | |
| 72 | Adrián Fierro | 4 | 2017-2032 | |
| 72 | Víctor García | 4 | 2023-2036 | |
| 72 | Roger Garrett | 4 | 2014-2024 | |
| 72 | Torvald Geertsen | 4 | 2018-2021 | |
| 72 | Natalino Golaio | 4 | 2022-2038 | |
| 72 | Jesús Gonzáles* | 4 | 2020-2031 | |
| 72 | Ricardo Gómez | 4 | 2023-2032 | |
| 72 | Woodward Haberdash# | 4 | 2034-2046 |
