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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | James Scott | 60 | 2022-2029 | |
| 2 | Jason McKinney | 57 | 2015-2024 | |
| 3 | Fernando González | 45 | 2017-2024 | |
| 4 | Cameron Frye | 44 | 2024-2034 | |
| 5 | Huai-yu Kan | 43 | 2015-2022 | |
| 6 | José Sánchez# | 41 | 2025-2037 | |
| 7 | Tomiji Saikawa | 39 | 2021-2024 | |
| 7 | Chris Sommer# | 39 | 2028-2034 | |
| 9 | Rodger de Meza | 38 | 2022-2026 | |
| 9 | Júlio Hernández | 38 | 2016-2025 | |
| 11 | Nate Rogers | 37 | 2017-2025 | |
| 11 | Edward Whipp | 37 | 2023-2029 | |
| 13 | Juan Lara | 36 | 2025-2029 | |
| 14 | Raúl Pérez | 35 | 2015-2025 | |
| 15 | Ron Barry | 34 | 2015-2019 | |
| 15 | Robinson Suárez# | 34 | 2025-2036 | |
| 17 | Aaron Wise | 33 | 2017-2023 | |
| 18 | Roberto Aguirre | 31 | 2022-2032 | |
| 18 | Bryan Houston | 31 | 2019-2026 | |
| 20 | Artie Chávez | 30 | 2022-2027 | |
| 20 | Kent Horton# | 30 | 2034-2037 | |
| 20 | Edgar Lankford | 30 | 2025-2030 | |
| 23 | Marv Bradford | 29 | 2027-2029 | |
| 23 | Ricardo Gómez | 29 | 2028-2034 | |
| 23 | Santiago López# | 29 | 2027-2037 | |
| 23 | Bartolo Ruíz# | 29 | 2030-2035 | |
| 23 | Francisco Sandoval | 29 | 2029-2034 | |
| 23 | Jeff Sloan | 29 | 2018-2022 | |
| 29 | Luis Cuero | 28 | 2025-2036 | |
| 29 | Robert Dickinson | 28 | 2015-2027 | |
| 29 | Dalton García | 28 | 2015-2032 | |
| 29 | Grant White | 28 | 2022-2028 | |
| 33 | Juan Cruz | 27 | 2021-2029 | |
| 33 | Orsino Lippi | 27 | 2018-2020 | |
| 33 | Rafael Méndez | 27 | 2029-2033 | |
| 33 | Santiago Mesa | 27 | 2024-2029 | |
| 33 | Jordan Turpin | 27 | 2029-2035 | |
| 38 | Lorenzo Díaz# | 26 | 2031-2037 | |
| 38 | Juan López | 26 | 2025-2033 | |
| 38 | Ron O'Slattery | 26 | 2015-2023 | |
| 41 | António Alomar# | 25 | 2028-2034 | |
| 41 | Cisco Andr | 25 | 2030-2036 | |
| 41 | António Marés# | 25 | 2034-2037 | |
| 41 | Júlio Martínez | 25 | 2025-2030 | |
| 41 | Bernie Sanders | 25 | 2025-2027 | |
| 41 | Xiao-shuang Wong# | 25 | 2032-2037 | |
| 47 | José Guillén# | 24 | 2033-2037 | |
| 47 | Ben Hopley | 24 | 2029-2032 | |
| 47 | John McCord | 24 | 2023-2028 | |
| 47 | Manny Pérez | 24 | 2024-2029 | |
| 47 | Juan Reyes | 24 | 2024-2028 | |
| 52 | Tony DeWitt | 23 | 2032-2036 | |
| 52 | Enea Dini | 23 | 2026-2029 | |
| 52 | Armando Gonzáles | 23 | 2023-2030 | |
| 52 | Kenny Kawaguchi# | 23 | 2030-2037 | |
| 52 | Mike Owens | 23 | 2027-2029 | |
| 52 | Suezo Sato | 23 | 2015-2020 | |
| 52 | Bastião Shwerin | 23 | 2026-2031 | |
| 59 | Casey Bader | 22 | 2022-2024 | |
| 59 | Tom Bowen | 22 | 2016-2019 | |
| 59 | Iwane Chihara | 22 | 2031-2034 | |
| 59 | Atila Freska# | 22 | 2031-2036 | |
| 59 | Nésto Gago# | 22 | 2031-2037 | |
| 59 | Cole Johnson | 22 | 2016-2020 | |
| 59 | Ben Logan | 22 | 2024-2031 | |
| 59 | Orlando Martínez | 22 | 2015-2025 | |
| 59 | Stanley Neal | 22 | 2021-2024 | |
| 59 | Tim Nelson | 22 | 2017-2019 | |
| 59 | Piotr Oja | 22 | 2027-2036 | |
| 59 | Alfredo Ríos | 22 | 2022-2027 | |
| 71 | Rio Bavin | 21 | 2026-2033 | |
| 71 | Jorge Cedeño# | 21 | 2027-2029 | |
| 71 | Eugene Clarkston | 21 | 2023-2034 | |
| 71 | Luis Gonzáles | 21 | 2017-2024 | |
| 71 | Donald Gregory | 21 | 2021-2032 | |
| 71 | Harry Mander | 21 | 2024-2030 | |
| 71 | Javier Romero# | 21 | 2029-2032 | |
| 71 | Russ Rose | 21 | 2017-2021 | |
| 71 | Ken Shelton | 21 | 2028-2033 | |
| 71 | Millard Taylor | 21 | 2027-2029 | |
| 71 | Gordon Wiggins | 21 | 2015-2025 | |
| 82 | Ingo Abresch# | 20 | 2036-2037 | |
| 82 | Alfonso Álvarez | 20 | 2023-2028 | |
| 82 | Alejandro Arteaga | 20 | 2022-2026 | |
| 82 | Michael Brown | 20 | 2024-2031 | |
| 82 | Connor Dale | 20 | 2020-2023 | |
| 82 | Chris Hayes | 20 | 2029-2035 | |
| 82 | Eric Newell | 20 | 2020-2024 | |
| 82 | Bob Payne | 20 | 2028-2032 | |
| 82 | Alberto Reyes | 20 | 2025-2030 | |
| 82 | Octávio Ríos | 20 | 2026-2029 | |
| 82 | Valentín Rivera | 20 | 2026-2031 | |
| 82 | Juan Sánchez# | 20 | 2034-2036 | |
| 82 | Gabriel Valenzuela# | 20 | 2031-2035 | |
| 95 | Lawrence Bignold | 19 | 2016-2026 | |
| 95 | Willie Cameron | 19 | 2023-2025 | |
| 95 | Jorge Cruzan# | 19 | 2031-2033 | |
| 95 | Manuel Delgado | 19 | 2016-2026 | |
| 95 | Hank Downey | 19 | 2017-2022 | |
| 95 | Raúl Gonzáles | 19 | 2029-2033 |
