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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Armando Ortíz | 43 | 2021-2025 | |
| 2 | Steve Baker | 35 | 2040-2044 | |
| 2 | Carl MacPherson | 35 | 2031-2035 | |
| 4 | Brad Hehir | 31 | 2045-2047 | |
| 5 | Joe Holland | 29 | 2034-2036 | |
| 6 | Pedro Adame | 28 | 2026-2028 | |
| 7 | Zach Pinyerrel | 27 | 2029-2034 | |
| 7 | Cristóbal Román | 27 | 2032-2034 | |
| 7 | Edward Scarborough | 27 | 2026-2029 | |
| 10 | Erik Illescas | 26 | 2031-2035 | |
| 10 | Santtu Öunap | 26 | 2031-2036 | |
| 12 | Loren Berdine | 25 | 2027-2029 | |
| 12 | Bob Browning | 25 | 2023-2025 | |
| 12 | Gabriel Escobar | 25 | 2022-2025 | |
| 12 | Felipe Pereira | 25 | 2024-2027 | |
| 16 | Kevin Beckman | 24 | 2032-2035 | |
| 16 | Umebayashi Naofumi | 24 | 2034-2038 | |
| 16 | Morihiro Sai | 24 | 2025-2027 | |
| 16 | Rusty Swanson | 24 | 2023-2025 | |
| 16 | Daisuke Yoshikawa# | 24 | 2046-2049 | |
| 21 | Luis Castillo# | 23 | 2045-2047 | |
| 21 | Kent Horton | 23 | 2030-2032 | |
| 21 | Brian Payne# | 23 | 2051-2053 | |
| 21 | Cisco Pérez | 23 | 2029-2030 | |
| 21 | Alejandro Ramos | 23 | 2021-2025 | |
| 21 | Tony Torres | 23 | 2031-2032 | |
| 27 | Francisco González | 22 | 2042-2045 | |
| 27 | Shaun Marchant# | 22 | 2049-2052 | |
| 27 | Gonzalo Montés | 22 | 2022-2026 | |
| 27 | Todd O'Looney# | 22 | 2052-2053 | |
| 27 | Bob O'Slattery# | 22 | 2051-2052 | |
| 27 | Juan Ramírez | 22 | 2043-2047 | |
| 27 | Donnie Rawling | 22 | 2034-2037 | |
| 27 | Nick Richie | 22 | 2022-2024 | |
| 27 | Yan Velthuizen# | 22 | 2050-2052 | |
| 36 | Paul Allen | 21 | 2046-2048 | |
| 36 | Francisco Burgos | 21 | 2025-2028 | |
| 36 | Dale Burney# | 21 | 2051-2052 | |
| 36 | Jeff Davis | 21 | 2039-2041 | |
| 36 | Dave Hamilton | 21 | 2037-2040 | |
| 36 | José López | 21 | 2026-2028 | |
| 36 | Albert Surtees# | 21 | 2047-2049 | |
| 43 | Benjamin Busto | 20 | 2025-2027 | |
| 43 | Harrison Dunning | 20 | 2030-2031 | |
| 43 | Justin Flynn | 20 | 2029-2030 | |
| 43 | Adrian Griffith | 20 | 2045-2047 | |
| 43 | Rémy Moreau | 20 | 2041-2046 | |
| 43 | Kewiki Pua | 20 | 2029-2030 | |
| 43 | Guillermo Quiñones | 20 | 2042-2046 | |
| 43 | Turner Shamburger | 20 | 2030-2033 | |
| 43 | Carlos Vidro# | 20 | 2049-2051 | |
| 43 | Dario Zorander | 20 | 2040-2042 | |
| 53 | Nicolas Cernin | 19 | 2043-2045 | |
| 53 | Phillip Donoghue | 19 | 2029-2033 | |
| 53 | Evan Groenevelt | 19 | 2031-2035 | |
| 53 | Charles Harvey | 19 | 2043-2045 | |
| 53 | Song-saeng Kim | 19 | 2021-2024 | |
| 53 | António Marés | 19 | 2021-2022 | |
| 53 | Burian Polyn# | 19 | 2045-2047 | |
| 53 | Ismael Riddles | 19 | 2033-2036 | |
| 53 | José Santiago | 19 | 2024-2027 | |
| 53 | Alberto Solís | 19 | 2025-2027 | |
| 53 | Josef Strolz | 19 | 2023-2025 | |
| 64 | Darius Baxa | 18 | 2025-2026 | |
| 64 | Jim Davis | 18 | 2021-2025 | |
| 64 | John Fleming | 18 | 2038-2039 | |
| 64 | Ramón Flores | 18 | 2035-2037 | |
| 64 | Al Gagne | 18 | 2034-2035 | |
| 64 | Ramiro García | 18 | 2022-2024 | |
| 64 | Chae-seong Kim | 18 | 2021-2022 | |
| 64 | Roberto Punyed | 18 | 2039-2042 | |
| 64 | Ánibal Rivera | 18 | 2020-2022 | |
| 64 | Victor Robertson | 18 | 2042-2044 | |
| 64 | Jon Shirley | 18 | 2023-2024 | |
| 64 | Javier Téllez | 18 | 2039-2042 | |
| 64 | Pleun Wolf# | 18 | 2050-2051 | |
| 64 | Paul Workman | 18 | 2035-2037 | |
| 78 | Jordon Glen Anderson | 17 | 2039-2041 | |
| 78 | Lawrence Anderson# | 17 | 2049-2051 | |
| 78 | Guus Danen | 17 | 2034-2036 | |
| 78 | Andy Fallon | 17 | 2029-2030 | |
| 78 | Li-zhi Lai# | 17 | 2048-2050 | |
| 78 | Van Lapointe | 17 | 2031-2035 | |
| 78 | Ismael Lara | 17 | 2024-2027 | |
| 78 | Ed Molloy | 17 | 2030-2033 | |
| 78 | Cisco Morales# | 17 | 2050-2051 | |
| 78 | James Neutron | 17 | 2024-2026 | |
| 78 | Richard Nudelman | 17 | 2042-2045 | |
| 78 | Miguel Núñez | 17 | 2037-2040 | |
| 78 | William Penn | 17 | 2032-2034 | |
| 78 | Jesús Ríos# | 17 | 2038-2040 | |
| 78 | Osiris St. Brown | 17 | 2027-2028 | |
| 78 | Yoshihide Sugiyama | 17 | 2044-2046 | |
| 78 | Tyrone Tolbert | 17 | 2047-2048 | |
| 78 | Jorge Travieso | 17 | 2028-2030 | |
| 96 | Ramón Cortéz | 16 | 2028-2032 | |
| 96 | Elijah Cox# | 16 | 2052-2053 | |
| 96 | António Fernández | 16 | 2030-2032 | |
| 96 | Shawn Hanna | 16 | 2039-2040 | |
| 96 | Luis Hernández | 16 | 2025-2026 |
