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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Victor Brey | 72 | 2021-2028 | |
| 2 | Willie Cameron | 54 | 2016-2031 | |
| 3 | Matt Davenport | 45 | 2029-2037 | |
| 4 | Luis Hernández | 43 | 2030-2037 | |
| 4 | Cisco Pérez | 43 | 2034-2038 | |
| 6 | Wop Baars | 41 | 2032-2041 | |
| 6 | Drew Cullen | 41 | 2027-2035 | |
| 8 | Mario Ruíz | 39 | 2023-2031 | |
| 9 | Miguel Cervantes | 38 | 2026-2038 | |
| 9 | Chae-seong Kim | 38 | 2023-2033 | |
| 11 | Salvador Sagastizabal | 37 | 2036-2043 | |
| 12 | Patrick Ibáñez# | 36 | 2035-2043 | |
| 13 | Claudio Díaz | 35 | 2022-2031 | |
| 13 | José Salinas | 35 | 2017-2027 | |
| 15 | Francisco Barrios | 34 | 2020-2033 | |
| 15 | Marvin Mangin | 34 | 2023-2028 | |
| 17 | Miguel Cabañas | 33 | 2029-2035 | |
| 17 | Fred Gunther | 33 | 2036-2040 | |
| 17 | Giovanni Mireles# | 33 | 2026-2043 | |
| 20 | Roy Alsobrook | 32 | 2028-2038 | |
| 20 | Miguel Álvarez | 32 | 2027-2033 | |
| 20 | Alejandro Araya | 32 | 2028-2039 | |
| 20 | Dennis Brown | 32 | 2022-2030 | |
| 20 | Earl Brown | 32 | 2023-2031 | |
| 20 | Antonio Godfrey | 32 | 2028-2033 | |
| 20 | Shunen Takahashi | 32 | 2022-2035 | |
| 27 | Jorge Cedeño | 31 | 2033-2037 | |
| 27 | Steve Costlow | 31 | 2032-2038 | |
| 27 | King Fletcher | 31 | 2023-2030 | |
| 27 | Artie Horton | 31 | 2022-2025 | |
| 27 | Louis McDowell | 31 | 2016-2028 | |
| 27 | José Ortíz | 31 | 2026-2037 | |
| 27 | Larry Strozier | 31 | 2030-2035 | |
| 27 | Joel Walden# | 31 | 2036-2043 | |
| 27 | Won-u Yi | 31 | 2029-2041 | |
| 36 | Raúl Andrés | 30 | 2016-2021 | |
| 36 | Dahab Kanda | 30 | 2029-2043 | |
| 36 | Bob Warford | 30 | 2018-2034 | |
| 39 | Lucas Begay | 29 | 2025-2028 | |
| 39 | Roberto Calderón | 29 | 2024-2035 | |
| 39 | Roberto Gómez | 29 | 2022-2031 | |
| 39 | Arturo Guerrero | 29 | 2028-2039 | |
| 39 | José Guillén | 29 | 2028-2030 | |
| 39 | Cris Herrera | 29 | 2022-2034 | |
| 39 | Sammy Nash | 29 | 2024-2029 | |
| 39 | Scott Thompson# | 29 | 2035-2038 | |
| 39 | Octávio Valdéz | 29 | 2033-2039 | |
| 48 | Frank Bryant | 28 | 2021-2028 | |
| 48 | Benjamin Busto | 28 | 2029-2038 | |
| 48 | Hervé Favier | 28 | 2028-2043 | |
| 48 | Ollie McDaniell | 28 | 2033-2037 | |
| 48 | Bobby Roode | 28 | 2031-2041 | |
| 48 | Doug Ryan | 28 | 2016-2024 | |
| 48 | Albert Sierra | 28 | 2034-2041 | |
| 48 | Liam Thomson# | 28 | 2032-2034 | |
| 56 | Gary Barber | 27 | 2021-2033 | |
| 56 | Eduardo Capata | 27 | 2019-2032 | |
| 56 | Jordan Coffey | 27 | 2035-2043 | |
| 56 | Carlos Díaz | 27 | 2030-2033 | |
| 56 | Hank Downey | 27 | 2021-2030 | |
| 56 | Norberto Flores | 27 | 2027-2033 | |
| 56 | Aurélien Godet | 27 | 2015-2023 | |
| 56 | Ralph Haggerty | 27 | 2029-2038 | |
| 56 | Ben Hopley | 27 | 2024-2034 | |
| 56 | José Marín | 27 | 2034-2041 | |
| 56 | Emil Olsson | 27 | 2027-2036 | |
| 56 | Gerrit Zuidgeest | 27 | 2035-2040 | |
| 68 | José Acevedo | 26 | 2013-2023 | |
| 68 | Norm Burris | 26 | 2016-2021 | |
| 68 | Logan Gregory | 26 | 2027-2035 | |
| 68 | Kabeya Kasongo# | 26 | 2034-2038 | |
| 68 | Arturo Mesa | 26 | 2037-2040 | |
| 68 | Silverberry Mouhon | 26 | 2037-2043 | |
| 68 | Ricardo Suárez | 26 | 2027-2032 | |
| 75 | Anastasio Cabanillas Jr.# | 25 | 2033-2036 | |
| 75 | Woo-suk Cho | 25 | 2031-2035 | |
| 75 | Roberto De La Cruz | 25 | 2024-2027 | |
| 75 | Wayne Downey | 25 | 2022-2025 | |
| 75 | Travis Grant | 25 | 2024-2034 | |
| 75 | Tony Hernández | 25 | 2016-2020 | |
| 75 | Emerson Horton# | 25 | 2039-2043 | |
| 75 | Pedro Lara | 25 | 2025-2028 | |
| 75 | Yoshi Minamoto | 25 | 2032-2036 | |
| 75 | Doruk Oyan | 25 | 2016-2018 | |
| 75 | Brian Scalabrine | 25 | 2027-2032 | |
| 75 | Harvey Wyles# | 25 | 2038-2043 | |
| 87 | Travis Carson | 24 | 2022-2032 | |
| 87 | Stanley Eldrige | 24 | 2027-2035 | |
| 87 | Enrique García | 24 | 2023-2034 | |
| 87 | Awad Mahmudnizhad | 24 | 2034-2042 | |
| 87 | Júlio Martínez | 24 | 2019-2028 | |
| 87 | Júlio Palma | 24 | 2019-2022 | |
| 87 | Henri Pollini | 24 | 2019-2030 | |
| 87 | Jeff Schneider | 24 | 2022-2028 | |
| 87 | Javier Soto# | 24 | 2040-2043 | |
| 87 | Jason Troughton | 24 | 2023-2027 | |
| 97 | Dave Conley | 23 | 2015-2018 | |
| 97 | Ezio Deodato | 23 | 2023-2033 | |
| 97 | Riley Evans | 23 | 2037-2042 | |
| 97 | Sam Groves | 23 | 2030-2034 |
