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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 | Ray Spencer | 30 | 2053-2055 | |
| 6 | Joe Holland | 29 | 2034-2036 | |
| 7 | Pedro Adame | 28 | 2026-2028 | |
| 7 | Todd O'Looney | 28 | 2052-2054 | |
| 9 | Zach Pinyerrel | 27 | 2029-2034 | |
| 9 | Cristóbal Román | 27 | 2032-2034 | |
| 9 | Edward Scarborough | 27 | 2026-2029 | |
| 12 | John Dodson# | 26 | 2059-2061 | |
| 12 | Erik Illescas | 26 | 2031-2035 | |
| 12 | Santtu Öunap | 26 | 2031-2036 | |
| 15 | Loren Berdine | 25 | 2027-2029 | |
| 15 | Bob Browning | 25 | 2023-2025 | |
| 15 | Gabriel Escobar | 25 | 2022-2025 | |
| 15 | Felipe Pereira | 25 | 2024-2027 | |
| 19 | Kevin Beckman | 24 | 2032-2035 | |
| 19 | Umebayashi Naofumi | 24 | 2034-2038 | |
| 19 | Morihiro Sai | 24 | 2025-2027 | |
| 19 | Rusty Swanson | 24 | 2023-2025 | |
| 19 | Daisuke Yoshikawa | 24 | 2046-2049 | |
| 24 | Luis Castillo | 23 | 2045-2047 | |
| 24 | Mark Cunningham# | 23 | 2053-2054 | |
| 24 | Kent Horton | 23 | 2030-2032 | |
| 24 | Brian Payne | 23 | 2051-2053 | |
| 24 | Cisco Pérez | 23 | 2029-2030 | |
| 24 | Alejandro Ramos | 23 | 2021-2025 | |
| 24 | Tony Torres | 23 | 2031-2032 | |
| 31 | Akil bin Abbud# | 22 | 2055-2057 | |
| 31 | Lonnie Burton | 22 | 2055-2057 | |
| 31 | Francisco González | 22 | 2042-2045 | |
| 31 | Jacob Harrell# | 22 | 2058-2060 | |
| 31 | Shaun Marchant | 22 | 2049-2052 | |
| 31 | Gonzalo Montés | 22 | 2022-2026 | |
| 31 | Bob O'Slattery | 22 | 2051-2052 | |
| 31 | Juan Ramírez | 22 | 2043-2047 | |
| 31 | Donnie Rawling | 22 | 2034-2037 | |
| 31 | Nick Richie | 22 | 2022-2024 | |
| 31 | Yan Velthuizen | 22 | 2050-2052 | |
| 42 | Paul Allen | 21 | 2046-2048 | |
| 42 | Francisco Burgos | 21 | 2025-2028 | |
| 42 | Dale Burney | 21 | 2051-2052 | |
| 42 | Juan Cervantes# | 21 | 2057-2059 | |
| 42 | Jeff Davis | 21 | 2039-2041 | |
| 42 | José Durán# | 21 | 2054-2055 | |
| 42 | Dave Hamilton | 21 | 2037-2040 | |
| 42 | José López | 21 | 2026-2028 | |
| 42 | Lúcio Patino# | 21 | 2057-2060 | |
| 42 | Albert Surtees | 21 | 2047-2049 | |
| 42 | Jesús Sánchez | 21 | 2053-2054 | |
| 42 | Vicente Torres# | 21 | 2058-2060 | |
| 42 | Franklin Vaughn# | 21 | 2058-2061 | |
| 55 | Benjamin Busto | 20 | 2025-2027 | |
| 55 | Harrison Dunning | 20 | 2030-2031 | |
| 55 | Justin Flynn | 20 | 2029-2030 | |
| 55 | Adrian Griffith | 20 | 2045-2047 | |
| 55 | Rémy Moreau | 20 | 2041-2046 | |
| 55 | Jang-jin Na# | 20 | 2060-2061 | |
| 55 | Kewiki Pua | 20 | 2029-2030 | |
| 55 | Guillermo Quiñones | 20 | 2042-2046 | |
| 55 | Turner Shamburger | 20 | 2030-2033 | |
| 55 | Carlos Vidro | 20 | 2049-2051 | |
| 55 | Dario Zorander | 20 | 2040-2042 | |
| 66 | Nicolas Cernin | 19 | 2043-2045 | |
| 66 | Phillip Donoghue | 19 | 2029-2033 | |
| 66 | Evan Groenevelt | 19 | 2031-2035 | |
| 66 | Charles Harvey | 19 | 2043-2045 | |
| 66 | Song-saeng Kim | 19 | 2021-2024 | |
| 66 | António Marés | 19 | 2021-2022 | |
| 66 | Burian Polyn | 19 | 2045-2047 | |
| 66 | Ismael Riddles | 19 | 2033-2036 | |
| 66 | José Santiago | 19 | 2024-2027 | |
| 66 | Alberto Solís | 19 | 2025-2027 | |
| 66 | Josef Strolz | 19 | 2023-2025 | |
| 66 | Shawn Wise | 19 | 2053-2055 | |
| 78 | Darius Baxa | 18 | 2025-2026 | |
| 78 | Jim Davis | 18 | 2021-2025 | |
| 78 | John Fleming | 18 | 2038-2039 | |
| 78 | Ramón Flores | 18 | 2035-2037 | |
| 78 | Al Gagne | 18 | 2034-2035 | |
| 78 | Ramiro García | 18 | 2022-2024 | |
| 78 | Chae-seong Kim | 18 | 2021-2022 | |
| 78 | Roberto Punyed | 18 | 2039-2042 | |
| 78 | Ánibal Rivera | 18 | 2020-2022 | |
| 78 | Victor Robertson | 18 | 2042-2044 | |
| 78 | Jon Shirley | 18 | 2023-2024 | |
| 78 | Javier Téllez | 18 | 2039-2042 | |
| 78 | Pleun Wolf | 18 | 2050-2051 | |
| 78 | Paul Workman | 18 | 2035-2037 | |
| 92 | Jordon Glen Anderson | 17 | 2039-2041 | |
| 92 | Lawrence Anderson | 17 | 2049-2051 | |
| 92 | Guus Danen | 17 | 2034-2036 | |
| 92 | Andy Fallon | 17 | 2029-2030 | |
| 92 | Li-zhi Lai | 17 | 2048-2050 | |
| 92 | Van Lapointe | 17 | 2031-2035 | |
| 92 | Ismael Lara | 17 | 2024-2027 | |
| 92 | Júlio Medina# | 17 | 2055-2057 | |
| 92 | Ed Molloy | 17 | 2030-2033 |
