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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Sebastiaan de Roode# | 9 | 2032-2033 | |
| 2 | Tsurayuki Harada# | 8 | 2029-2040 | |
| 3 | Andrew Burns | 6 | 2021-2033 | |
| 3 | Skip Hathaway# | 6 | 2033-2036 | |
| 3 | Adam Pemberton# | 6 | 2027-2040 | |
| 3 | Barney Swanson# | 6 | 2027-2038 | |
| 7 | Brock Barrett | 5 | 2012-2025 | |
| 7 | Mauro Bustamante# | 5 | 2035-2040 | |
| 7 | Pasquale Richelmi# | 5 | 2035-2039 | |
| 10 | Felipe Aguilera# | 4 | 2037-2040 | |
| 10 | Marcos Alcorta | 4 | 2025-2030 | |
| 10 | Jim Fish | 4 | 2024-2037 | |
| 10 | Luis Miguel Freitas# | 4 | 2035-2040 | |
| 10 | Robinson Hernández# | 4 | 2028-2038 | |
| 10 | Min-zhong Lou# | 4 | 2034-2035 | |
| 10 | Michael Mooney# | 4 | 2038-2040 | |
| 10 | Andrés Rodríguez# | 4 | 2030-2030 | |
| 10 | Roberto Ruíz# | 4 | 2034-2036 | |
| 10 | Kyle Tatham | 4 | 2025-2026 | |
| 10 | Pedro Torres# | 4 | 2027-2040 | |
| 10 | León Vallés | 4 | 2009-2013 | |
| 22 | Tommy Atkins# | 3 | 2036-2037 | |
| 22 | Arlen Badger# | 3 | 2027-2039 | |
| 22 | Ángel Borges# | 3 | 2039-2039 | |
| 22 | Lou Butler# | 3 | 2029-2040 | |
| 22 | Héctor Colomo# | 3 | 2033-2037 | |
| 22 | Félix Córdova | 3 | 2023-2035 | |
| 22 | Roderick Davis | 3 | 2033-2033 | |
| 22 | Robbie Dupuis# | 3 | 2028-2040 | |
| 22 | Jorge Flores# | 3 | 2033-2034 | |
| 22 | José Flores# | 3 | 2034-2034 | |
| 22 | Fernando García | 3 | 2032-2035 | |
| 22 | Alonso González# | 3 | 2034-2040 | |
| 22 | José González | 3 | 2013-2022 | |
| 22 | Oliver González | 3 | 2014-2016 | |
| 22 | Izumo Kondo | 3 | 2025-2031 | |
| 22 | Emílio Martínez# | 3 | 2032-2037 | |
| 22 | Luis Nieves | 3 | 2032-2032 | |
| 22 | Millard Norman | 3 | 2024-2024 | |
| 22 | René Padilla# | 3 | 2034-2034 | |
| 22 | Juan Jose Patino | 3 | 2024-2038 | |
| 22 | Alfredo Reyes | 3 | 2027-2036 | |
| 22 | Joe Russell# | 3 | 2028-2037 | |
| 22 | Eisuke Sanu | 3 | 2020-2023 | |
| 22 | Seong-chae Somun# | 3 | 2029-2039 | |
| 22 | Shigenobu Taguchi | 3 | 2025-2039 | |
| 22 | Orlando Trujillo# | 3 | 2026-2027 | |
| 22 | Huibrecht Ubbens | 3 | 2032-2036 | |
| 22 | Erik Watson | 3 | 2024-2039 | |
| 22 | Robby Wiggins | 3 | 2029-2029 | |
| 22 | Yuji Yamashita# | 3 | 2032-2033 | |
| 52 | Arnold Adams# | 2 | 2034-2035 | |
| 52 | Phil Anderson | 2 | 2012-2014 | |
| 52 | Lewis Bedser# | 2 | 2034-2034 | |
| 52 | Fred Benjamin | 2 | 2012-2029 | |
| 52 | Kenny Boone# | 2 | 2038-2038 | |
| 52 | Shawn Burris | 2 | 2007-2011 | |
| 52 | Kurt Cameron# | 2 | 2036-2038 | |
| 52 | Jason Campbell | 2 | 2020-2025 | |
| 52 | Martin Cantin | 2 | 2012-2012 | |
| 52 | Luis Cavazos# | 2 | 2035-2036 | |
| 52 | Hyo-cheong Cho# | 2 | 2037-2038 | |
| 52 | José Chávez | 2 | 2012-2015 | |
| 52 | Henry Cluett# | 2 | 2029-2030 | |
| 52 | Jake Conrad# | 2 | 2030-2037 | |
| 52 | Allen Cook | 2 | 2024-2038 | |
| 52 | Tony Correa# | 2 | 2037-2037 | |
| 52 | Dimião Cortes# | 2 | 2037-2038 | |
| 52 | Jesús Cruz | 2 | 2019-2022 | |
| 52 | Takejiro Daikawa | 2 | 2029-2029 | |
| 52 | Luis De La Gara# | 2 | 2032-2036 | |
| 52 | Luis Durán | 2 | 2021-2026 | |
| 52 | Zander Eichhorn | 2 | 2009-2011 | |
| 52 | Luis García | 2 | 2019-2019 | |
| 52 | Pedro González | 2 | 2029-2030 | |
| 52 | Flávio Guedaz# | 2 | 2038-2040 | |
| 52 | Juan Guerrero# | 2 | 2030-2030 | |
| 52 | Todd Gustafson | 2 | 2029-2029 | |
| 52 | Manuel Gómez | 2 | 2010-2012 | |
| 52 | Jorge Hart# | 2 | 2030-2040 | |
| 52 | Juan Hernández | 2 | 2023-2035 | |
| 52 | Richard Higgins# | 2 | 2032-2032 | |
| 52 | Christian Hill | 2 | 2014-2023 | |
| 52 | Soetsu Hirai | 2 | 2022-2024 | |
| 52 | Rusty Hughes# | 2 | 2037-2038 | |
| 52 | Hiroya Ishikawa | 2 | 2033-2035 | |
| 52 | Colin Jameson | 2 | 2022-2027 | |
| 52 | Juan Jaramillo# | 2 | 2033-2034 | |
| 52 | Ahmad Jitu# | 2 | 2035-2039 | |
| 52 | Allen Johnson | 2 | 2014-2023 | |
| 52 | Jim Jones# | 2 | 2026-2028 | |
| 52 | Rich Jones# | 2 | 2033-2033 | |
| 52 | Gerardo Juárez | 2 | 2026-2030 | |
| 52 | Iemitsu Kato# | 2 | 2035-2037 | |
| 52 | Charles Kennedy | 2 | 2016-2019 | |
| 52 | Dong-min Kim# | 2 | 2028-2034 | |
| 52 | Ryozo Kono | 2 | 2027-2035 | |
| 52 | Rick Lewis# | 2 | 2038-2038 | |
| 52 | Jesús López# | 2 | 2038-2038 | |
| 52 | Finlay MacEwan# | 2 | 2037-2038 |
