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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 | Travis Morgan | 8 | 2039-2049 | |
| 10 | Jay Newton# | 8 | 2042-2052 | |
| 10 | Chase Sims | 8 | 2039-2049 | |
| 10 | Juan Torres | 8 | 2021-2032 | |
| 17 | Rafael Cardona | 7 | 2022-2035 | |
| 17 | Matthew Fallows | 7 | 2034-2048 | |
| 17 | Janghyun Han# | 7 | 2044-2053 | |
| 17 | Cris Mendoza | 7 | 2017-2029 | |
| 17 | Kevin Nogilny | 7 | 2032-2046 | |
| 17 | Jorge Otero* | 7 | 2030-2040 | |
| 17 | Elroy Thompkins | 7 | 2029-2043 | |
| 17 | Bill Tugwell | 7 | 2029-2034 | |
| 25 | Robbie Baxter | 6 | 2022-2037 | |
| 25 | Dave Becker# | 6 | 2040-2053 | |
| 25 | Magnus Belli# | 6 | 2040-2051 | |
| 25 | Alfonso Caballero | 6 | 2038-2051 | |
| 25 | Kent Clement | 6 | 2022-2033 | |
| 25 | David Collingwood | 6 | 2019-2028 | |
| 25 | John Dempsey | 6 | 2022-2036 | |
| 25 | Juan Díaz | 6 | 2025-2036 | |
| 25 | Zaki Fakhiri | 6 | 2034-2046 | |
| 25 | George Frazier | 6 | 2017-2036 | |
| 25 | Juan Guillén* | 6 | 2027-2039 | |
| 25 | Cole Hall | 6 | 2016-2027 | |
| 25 | John Holley | 6 | 2014-2022 | |
| 25 | Tsugahara Hori | 6 | 2029-2040 | |
| 25 | Anatoly Ivanovich | 6 | 2030-2039 | |
| 25 | Bartolomeu Lio | 6 | 2019-2034 | |
| 25 | Jeff Mahl | 6 | 2035-2046 | |
| 25 | Lou Meadows | 6 | 2016-2027 | |
| 25 | José Quiñones | 6 | 2034-2043 | |
| 25 | Roderick Rhodes | 6 | 2017-2028 | |
| 25 | Cory Sanders | 6 | 2021-2036 | |
| 25 | Quintiliano Seixal | 6 | 2025-2037 | |
| 25 | Pedro Valdéz | 6 | 2020-2040 | |
| 25 | Jesús Vidro | 6 | 2033-2045 | |
| 49 | Javier Ariza# | 5 | 2040-2053 | |
| 49 | Gary Bailey* | 5 | 2022-2031 | |
| 49 | John Brown | 5 | 2016-2031 | |
| 49 | Kjeld Burger# | 5 | 2048-2054 | |
| 49 | Pat Butler# | 5 | 2045-2053 | |
| 49 | Juan Contreras | 5 | 2030-2042 | |
| 49 | Dorian Daly | 5 | 2028-2036 | |
| 49 | Pablo De La Torre | 5 | 2022-2036 | |
| 49 | Manuel Delgadillo | 5 | 2028-2038 | |
| 49 | Virgil Dickerson# | 5 | 2043-2053 | |
| 49 | Paul Díaz | 5 | 2019-2030 | |
| 49 | Craig Fitzgerald | 5 | 2036-2050 | |
| 49 | Stewart Fleming | 5 | 2029-2033 | |
| 49 | Jesús Franco | 5 | 2028-2034 | |
| 49 | Ronald Fritz# | 5 | 2045-2052 | |
| 49 | Mario Gonzáles# | 5 | 2045-2052 | |
| 49 | Raúl Gómez | 5 | 2026-2034 | |
| 49 | Henry Hall | 5 | 2015-2026 | |
| 49 | Van Hileman# | 5 | 2041-2049 | |
| 49 | Hong-bin Hua | 5 | 2037-2046 | |
| 49 | Wayne Hurst | 5 | 2015-2028 | |
| 49 | Masami Kogawa | 5 | 2031-2034 | |
| 49 | Nam-shik Kwak | 5 | 2038-2047 | |
| 49 | Edison Larson | 5 | 2020-2038 | |
| 49 | Raúl Luna | 5 | 2028-2036 | |
| 49 | Michael Machen* | 5 | 2029-2041 | |
| 49 | Pat Martin# | 5 | 2043-2053 | |
| 49 | Eric Matson* | 5 | 2027-2041 | |
| 49 | Francis McBride | 5 | 2023-2027 | |
| 49 | Gerardo Pagán | 5 | 2027-2036 | |
| 49 | Milutin Panic# | 5 | 2040-2046 | |
| 49 | Maru Pao Pao | 5 | 2029-2037 | |
| 49 | Chris Plautz# | 5 | 2043-2049 | |
| 49 | Joe Pruitt | 5 | 2031-2039 | |
| 49 | Domingo Ramírez | 5 | 2022-2039 | |
| 49 | Sylvain Richard# | 5 | 2042-2054 | |
| 49 | César Sandoval | 5 | 2038-2048 | |
| 49 | Lorenzo Sánchez | 5 | 2020-2033 | |
| 49 | Stanley Yelnats | 5 | 2030-2038 | |
| 88 | Art Adams | 4 | 2020-2031 | |
| 88 | José Alaniz | 4 | 2020-2030 | |
| 88 | Gary Ashley | 4 | 2034-2048 | |
| 88 | Luqman Barcoo | 4 | 2032-2035 | |
| 88 | Hermenegildo Beliago | 4 | 2027-2043 | |
| 88 | Faisal bin Nabeel | 4 | 2034-2041 | |
| 88 | Allen Blair | 4 | 2015-2032 | |
| 88 | Kyle Boddy | 4 | 2026-2034 | |
| 88 | Sjaak Bonne | 4 | 2027-2041 | |
| 88 | Quentin Bowers | 4 | 2028-2038 | |
| 88 | John Braun | 4 | 2014-2022 | |
| 88 | Jeremy Brody | 4 | 2042-2048 | |
| 88 | José Cotilla | 4 | 2032-2041 |
