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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 | 2034-2044 | |
| 14 | Cris Mendoza | 7 | 2017-2029 | |
| 14 | Jorge Otero | 7 | 2030-2040 | |
| 14 | Elroy Thompkins | 7 | 2029-2043 | |
| 14 | Bill Tugwell | 7 | 2029-2034 | |
| 20 | Robbie Baxter | 6 | 2022-2037 | |
| 20 | Kent Clement | 6 | 2022-2033 | |
| 20 | David Collingwood | 6 | 2019-2028 | |
| 20 | John Dempsey | 6 | 2022-2036 | |
| 20 | Juan Díaz | 6 | 2025-2036 | |
| 20 | George Frazier | 6 | 2017-2036 | |
| 20 | Juan Guillén | 6 | 2027-2039 | |
| 20 | Cole Hall | 6 | 2016-2027 | |
| 20 | John Holley | 6 | 2014-2022 | |
| 20 | Tsugahara Hori | 6 | 2029-2040 | |
| 20 | Anatoly Ivanovich | 6 | 2030-2039 | |
| 20 | Bartolomeu Lio | 6 | 2019-2034 | |
| 20 | Jeff Mahl# | 6 | 2035-2043 | |
| 20 | Lou Meadows | 6 | 2016-2027 | |
| 20 | Kevin Nogilny# | 6 | 2032-2043 | |
| 20 | José Quiñones | 6 | 2034-2043 | |
| 20 | Roderick Rhodes | 6 | 2017-2028 | |
| 20 | Cory Sanders | 6 | 2021-2036 | |
| 20 | Quintiliano Seixal | 6 | 2025-2037 | |
| 20 | Chase Sims# | 6 | 2039-2044 | |
| 20 | Pedro Valdéz | 6 | 2020-2040 | |
| 20 | Jesús Vidro# | 6 | 2033-2044 | |
| 42 | Gary Bailey* | 5 | 2022-2031 | |
| 42 | John Brown | 5 | 2016-2031 | |
| 42 | Juan Contreras | 5 | 2030-2042 | |
| 42 | Dorian Daly | 5 | 2028-2036 | |
| 42 | Pablo De La Torre | 5 | 2022-2036 | |
| 42 | Manuel Delgadillo | 5 | 2028-2038 | |
| 42 | Paul Díaz | 5 | 2019-2030 | |
| 42 | Zaki Fakhiri# | 5 | 2034-2042 | |
| 42 | Stewart Fleming | 5 | 2029-2033 | |
| 42 | Jesús Franco | 5 | 2028-2034 | |
| 42 | Raúl Gómez | 5 | 2026-2034 | |
| 42 | Henry Hall | 5 | 2015-2026 | |
| 42 | Hong-bin Hua# | 5 | 2037-2042 | |
| 42 | Wayne Hurst | 5 | 2015-2028 | |
| 42 | Masami Kogawa | 5 | 2031-2034 | |
| 42 | Edison Larson | 5 | 2020-2038 | |
| 42 | Raúl Luna | 5 | 2028-2036 | |
| 42 | Michael Machen | 5 | 2029-2041 | |
| 42 | Eric Matson | 5 | 2027-2041 | |
| 42 | Francis McBride | 5 | 2023-2027 | |
| 42 | Gerardo Pagán | 5 | 2027-2036 | |
| 42 | Maru Pao Pao | 5 | 2029-2037 | |
| 42 | Joe Pruitt | 5 | 2031-2039 | |
| 42 | Domingo Ramírez | 5 | 2022-2039 | |
| 42 | Lorenzo Sánchez | 5 | 2020-2033 | |
| 42 | Stanley Yelnats | 5 | 2030-2038 | |
| 68 | Art Adams | 4 | 2020-2031 | |
| 68 | José Alaniz | 4 | 2020-2030 | |
| 68 | Gary Ashley# | 4 | 2034-2044 | |
| 68 | Luqman Barcoo | 4 | 2032-2035 | |
| 68 | Dave Becker# | 4 | 2040-2044 | |
| 68 | Hermenegildo Beliago | 4 | 2027-2043 | |
| 68 | Faisal bin Nabeel | 4 | 2034-2041 | |
| 68 | Allen Blair | 4 | 2015-2032 | |
| 68 | Kyle Boddy | 4 | 2026-2034 | |
| 68 | Sjaak Bonne | 4 | 2027-2041 | |
| 68 | Quentin Bowers | 4 | 2028-2038 | |
| 68 | John Braun | 4 | 2014-2022 | |
| 68 | Alfonso Caballero# | 4 | 2038-2044 | |
| 68 | José Cotilla | 4 | 2032-2041 | |
| 68 | Billy Crawford | 4 | 2017-2025 | |
| 68 | Joe Crown | 4 | 2015-2026 | |
| 68 | Kenete Daku | 4 | 2029-2039 | |
| 68 | Paul Dudding | 4 | 2033-2038 | |
| 68 | Urs Ehles# | 4 | 2036-2044 | |
| 68 | Lorenzo Fabián | 4 | 2029-2041 | |
| 68 | Adrián Fierro | 4 | 2017-2032 | |
| 68 | Craig Fitzgerald# | 4 | 2036-2044 | |
| 68 | Víctor García | 4 | 2023-2036 | |
| 68 | Roger Garrett | 4 | 2014-2024 | |
| 68 | Torvald Geertsen | 4 | 2018-2021 | |
| 68 | Natalino Golaio | 4 | 2022-2038 | |
| 68 | Ricardo Gómez | 4 | 2023-2032 | |
| 68 | Jesús Gonzáles* | 4 | 2020-2031 | |
| 68 | Woodward Haberdash# | 4 | 2034-2044 | |
| 68 | Jackson Haines | 4 | 2014-2029 | |
| 68 | Jeff Hale | 4 | 2014-2027 | |
| 68 | Russ Horne | 4 | 2027-2037 | |
| 68 | Félix Jiménez | 4 | 2018-2028 |
