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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Pat Hunt | 50 | 2017-2029 | |
| 2 | Juan Pérez | 38 | 2017-2023 | |
| 3 | Daryl Benstead | 37 | 2042-2047 | |
| 4 | Lance de Valk | 35 | 2025-2030 | |
| 4 | Maurice Richards | 35 | 2054-2057 | |
| 4 | Bill Tennant | 35 | 2039-2042 | |
| 7 | John Ball | 34 | 2023-2031 | |
| 7 | Ken Carter | 34 | 2017-2025 | |
| 9 | Carlos Hernández | 33 | 2021-2028 | |
| 9 | Calle Lagerkvist | 33 | 2036-2043 | |
| 11 | César González | 31 | 2020-2029 | |
| 11 | Ronald Love | 31 | 2045-2048 | |
| 11 | Kliment Spirk | 31 | 2031-2036 | |
| 14 | Joe Holland | 30 | 2034-2040 | |
| 15 | Nicolas Cernin | 29 | 2046-2051 | |
| 15 | Hildo van Doorn | 29 | 2040-2042 | |
| 17 | Edward Lamb | 28 | 2057-2061 | |
| 17 | Ben Logan | 28 | 2019-2023 | |
| 19 | Shawn Arnold | 27 | 2017-2020 | |
| 19 | Luis Castrejón | 27 | 2024-2029 | |
| 19 | Paco Hernández | 27 | 2021-2027 | |
| 19 | George Hill# | 27 | 2053-2056 | |
| 19 | Aurelio López | 27 | 2019-2021 | |
| 19 | Leif Mayer | 27 | 2024-2029 | |
| 19 | Vince Moran | 27 | 2057-2060 | |
| 19 | Osiris St. Brown | 27 | 2032-2035 | |
| 19 | Gaberiela Tatafu | 27 | 2040-2043 | |
| 19 | Manuel Villalobos | 27 | 2046-2053 | |
| 29 | Norberto Concepción | 26 | 2029-2032 | |
| 29 | Foeke Reus | 26 | 2042-2047 | |
| 29 | Homer Sanders | 26 | 2045-2048 | |
| 29 | Yoshihide Sugiyama | 26 | 2044-2049 | |
| 29 | Jesús Sánchez | 26 | 2055-2057 | |
| 29 | Stanley Williams | 26 | 2017-2020 | |
| 35 | José Colón | 25 | 2034-2040 | |
| 35 | Severiano Duclos | 25 | 2018-2021 | |
| 35 | Pedro Reynoso | 25 | 2029-2032 | |
| 35 | Byron Rosebotham | 25 | 2029-2034 | |
| 35 | Mang Zhong | 25 | 2042-2048 | |
| 40 | Johnnie Bough | 24 | 2026-2032 | |
| 40 | Roberto Cabrera | 24 | 2037-2040 | |
| 40 | Aaron Ellicott | 24 | 2057-2059 | |
| 40 | John Hamilton | 24 | 2017-2027 | |
| 40 | Pat Horton | 24 | 2021-2022 | |
| 40 | Jesús López | 24 | 2015-2021 | |
| 40 | José López | 24 | 2032-2035 | |
| 40 | Mathieu Neri | 24 | 2024-2033 | |
| 40 | Héctor Peña | 24 | 2054-2055 | |
| 40 | Oliver Quested | 24 | 2050-2055 | |
| 40 | Ánibal Ramos# | 24 | 2058-2061 | |
| 40 | José Sandoval# | 24 | 2059-2062 | |
| 40 | Arthur Stevenson | 24 | 2042-2045 | |
| 40 | Lester Sullivan | 24 | 2018-2020 | |
| 40 | Daisuke Yoshikawa | 24 | 2048-2053 | |
| 55 | Heath Brown | 23 | 2040-2041 | |
| 55 | Dan Carter | 23 | 2043-2045 | |
| 55 | Jeff Cox | 23 | 2018-2021 | |
| 55 | Mike Foltynewicz | 23 | 2026-2028 | |
| 55 | Ken French | 23 | 2034-2039 | |
| 55 | Kazuchika Okada | 23 | 2034-2036 | |
| 55 | Jorge Ortíz | 23 | 2052-2056 | |
| 55 | Titus Parson | 23 | 2023-2027 | |
| 63 | Fernando Elías | 22 | 2031-2034 | |
| 63 | Hirokichi Kichida | 22 | 2018-2020 | |
| 63 | Hercules Mata'afa | 22 | 2031-2035 | |
| 63 | Jeff Morehead | 22 | 2047-2049 | |
| 63 | Doruk Oyan | 22 | 2020-2022 | |
| 63 | Donnie Rawling | 22 | 2038-2041 | |
| 63 | Don Swift# | 22 | 2059-2062 | |
| 63 | Arturo Sánchez | 22 | 2044-2047 | |
| 63 | Yuan Thian | 22 | 2046-2048 | |
| 72 | Alje Anraad | 21 | 2052-2054 | |
| 72 | Devoid Couch | 21 | 2038-2039 | |
| 72 | Jamey Crockett | 21 | 2030-2033 | |
| 72 | Ramón Flores | 21 | 2037-2039 | |
| 72 | Christian Harris | 21 | 2025-2029 | |
| 72 | Maxime Janssens | 21 | 2026-2027 | |
| 72 | Doyle Manning# | 21 | 2060-2061 | |
| 72 | Ollie McDaniell | 21 | 2031-2032 | |
| 72 | Walt Middleton | 21 | 2048-2051 | |
| 72 | Adam Oldenkamp | 21 | 2030-2033 | |
| 72 | Luis Ortíz | 21 | 2020-2026 | |
| 72 | Ed Pearce | 21 | 2046-2049 | |
| 72 | Joseph Reed | 21 | 2018-2023 | |
| 72 | Josh Reynolds | 21 | 2046-2051 | |
| 72 | Luke Robb | 21 | 2049-2051 | |
| 87 | Darius Baxa | 20 | 2027-2028 | |
| 87 | David Brandon | 20 | 2053-2056 | |
| 87 | Jorge Carrión | 20 | 2020-2025 | |
| 87 | Rob Dougherty | 20 | 2054-2057 | |
| 87 | Joel Farrell | 20 | 2030-2031 | |
| 87 | Tom Gaillard | 20 | 2015-2018 | |
| 87 | Mark Hogan | 20 | 2048-2052 | |
| 87 | Hong-bin Hua | 20 | 2033-2034 | |
| 87 | Teddy Jones | 20 | 2020-2022 | |
| 87 | Joaquín Martínez | 20 | 2058-2061 | |
| 87 | Tomás Mata | 20 | 2039-2041 | |
| 87 | Kyle McPherson | 20 | 2018-2023 | |
| 87 | Phil Miller | 20 | 2026-2028 | |
| 87 | Wally Moon | 20 | 2043-2047 |
