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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 | Bill Tennant | 35 | 2039-2042 | |
| 6 | John Ball | 34 | 2023-2031 | |
| 6 | Ken Carter | 34 | 2017-2025 | |
| 8 | Carlos Hernández | 33 | 2021-2028 | |
| 8 | Calle Lagerkvist | 33 | 2036-2043 | |
| 10 | César González | 31 | 2020-2029 | |
| 10 | Ronald Love# | 31 | 2045-2048 | |
| 10 | Kliment Spirk | 31 | 2031-2036 | |
| 13 | Joe Holland | 30 | 2034-2040 | |
| 14 | Nicolas Cernin# | 29 | 2046-2051 | |
| 14 | Hildo van Doorn | 29 | 2040-2042 | |
| 16 | Ben Logan | 28 | 2019-2023 | |
| 17 | Shawn Arnold | 27 | 2017-2020 | |
| 17 | Luis Castrejón | 27 | 2024-2029 | |
| 17 | Paco Hernández | 27 | 2021-2027 | |
| 17 | Aurelio López | 27 | 2019-2021 | |
| 17 | Leif Mayer | 27 | 2024-2029 | |
| 17 | Osiris St. Brown | 27 | 2032-2035 | |
| 17 | Gaberiela Tatafu | 27 | 2040-2043 | |
| 24 | Norberto Concepción | 26 | 2029-2032 | |
| 24 | Foeke Reus | 26 | 2042-2047 | |
| 24 | Homer Sanders# | 26 | 2045-2048 | |
| 24 | Yoshihide Sugiyama | 26 | 2044-2049 | |
| 24 | Stanley Williams | 26 | 2017-2020 | |
| 29 | José Colón | 25 | 2034-2040 | |
| 29 | Severiano Duclos | 25 | 2018-2021 | |
| 29 | Pedro Reynoso | 25 | 2029-2032 | |
| 29 | Byron Rosebotham | 25 | 2029-2034 | |
| 29 | Mang Zhong# | 25 | 2042-2048 | |
| 34 | Johnnie Bough | 24 | 2026-2032 | |
| 34 | Roberto Cabrera | 24 | 2037-2040 | |
| 34 | John Hamilton | 24 | 2017-2027 | |
| 34 | Pat Horton | 24 | 2021-2022 | |
| 34 | Jesús López | 24 | 2015-2021 | |
| 34 | José López | 24 | 2032-2035 | |
| 34 | Mathieu Neri | 24 | 2024-2033 | |
| 34 | Arthur Stevenson# | 24 | 2042-2045 | |
| 34 | Lester Sullivan | 24 | 2018-2020 | |
| 43 | Heath Brown# | 23 | 2040-2041 | |
| 43 | Dan Carter# | 23 | 2043-2045 | |
| 43 | Jeff Cox | 23 | 2018-2021 | |
| 43 | Mike Foltynewicz | 23 | 2026-2028 | |
| 43 | Ken French | 23 | 2034-2039 | |
| 43 | Kazuchika Okada | 23 | 2034-2036 | |
| 43 | Titus Parson | 23 | 2023-2027 | |
| 50 | Fernando Elías | 22 | 2031-2034 | |
| 50 | Hirokichi Kichida | 22 | 2018-2020 | |
| 50 | Hercules Mata'afa | 22 | 2031-2035 | |
| 50 | Jeff Morehead# | 22 | 2047-2049 | |
| 50 | Doruk Oyan | 22 | 2020-2022 | |
| 50 | Donnie Rawling | 22 | 2038-2041 | |
| 50 | Arturo Sánchez | 22 | 2044-2047 | |
| 50 | Yuan Thian# | 22 | 2046-2048 | |
| 58 | Devoid Couch | 21 | 2038-2039 | |
| 58 | Jamey Crockett | 21 | 2030-2033 | |
| 58 | Ramón Flores | 21 | 2037-2039 | |
| 58 | Christian Harris | 21 | 2025-2029 | |
| 58 | Maxime Janssens | 21 | 2026-2027 | |
| 58 | Ollie McDaniell | 21 | 2031-2032 | |
| 58 | Walt Middleton# | 21 | 2048-2051 | |
| 58 | Adam Oldenkamp | 21 | 2030-2033 | |
| 58 | Luis Ortíz | 21 | 2020-2026 | |
| 58 | Ed Pearce# | 21 | 2046-2049 | |
| 58 | Joseph Reed | 21 | 2018-2023 | |
| 58 | Josh Reynolds# | 21 | 2046-2051 | |
| 58 | Luke Robb# | 21 | 2049-2051 | |
| 71 | Darius Baxa | 20 | 2027-2028 | |
| 71 | Jorge Carrión | 20 | 2020-2025 | |
| 71 | Joel Farrell | 20 | 2030-2031 | |
| 71 | Tom Gaillard | 20 | 2015-2018 | |
| 71 | Hong-bin Hua | 20 | 2033-2034 | |
| 71 | Teddy Jones | 20 | 2020-2022 | |
| 71 | Tomás Mata | 20 | 2039-2041 | |
| 71 | Kyle McPherson | 20 | 2018-2023 | |
| 71 | Phil Miller | 20 | 2026-2028 | |
| 71 | Wally Moon | 20 | 2043-2047 | |
| 71 | César Morales | 20 | 2039-2042 | |
| 71 | Carlos Méndez | 20 | 2019-2020 | |
| 71 | Aurelio Ortíz | 20 | 2036-2040 | |
| 71 | Anil Seshu | 20 | 2045-2051 | |
| 85 | Art Adams | 19 | 2017-2019 | |
| 85 | Theodosio Brederode | 19 | 2042-2046 | |
| 85 | Benjamin Brouwer | 19 | 2021-2022 | |
| 85 | Francisco Díaz# | 19 | 2043-2049 | |
| 85 | William Gordon# | 19 | 2044-2047 | |
| 85 | Javier Mena | 19 | 2026-2032 | |
| 85 | Pablo Montoya# | 19 | 2046-2049 | |
| 85 | Pedro Montáñez | 19 | 2041-2044 | |
| 85 | Ramón Ocegueda | 19 | 2029-2032 | |
| 85 | Doppo Omikado | 19 | 2029-2032 | |
| 85 | Dave Seals | 19 | 2025-2028 | |
| 85 | Dave Shepard | 19 | 2039-2041 | |
| 85 | Chris Small# | 19 | 2048-2051 | |
| 85 | Lawrence Swift | 19 | 2034-2039 | |
| 85 | Vernon Turner | 19 | 2023-2027 | |
| 85 | António Uribe | 19 | 2018-2021 |
