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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 | Lance de Valk | 35 | 2025-2030 | |
| 4 | John Ball | 34 | 2023-2031 | |
| 4 | Ken Carter | 34 | 2017-2025 | |
| 6 | Carlos Hernández | 33 | 2021-2028 | |
| 7 | César González | 31 | 2020-2029 | |
| 7 | Kliment Spirk# | 31 | 2031-2036 | |
| 9 | Ben Logan | 28 | 2019-2023 | |
| 10 | Shawn Arnold | 27 | 2017-2020 | |
| 10 | Luis Castrejón | 27 | 2024-2029 | |
| 10 | Paco Hernández | 27 | 2021-2027 | |
| 10 | Aurelio López | 27 | 2019-2021 | |
| 10 | Leif Mayer | 27 | 2024-2029 | |
| 10 | Osiris St. Brown | 27 | 2032-2035 | |
| 16 | Norberto Concepción | 26 | 2029-2032 | |
| 16 | Stanley Williams | 26 | 2017-2020 | |
| 18 | Severiano Duclos | 25 | 2018-2021 | |
| 18 | Pedro Reynoso | 25 | 2029-2032 | |
| 18 | Byron Rosebotham# | 25 | 2029-2034 | |
| 21 | Johnnie Bough | 24 | 2026-2032 | |
| 21 | John Hamilton | 24 | 2017-2027 | |
| 21 | Joe Holland# | 24 | 2034-2038 | |
| 21 | Pat Horton | 24 | 2021-2022 | |
| 21 | Jesús López | 24 | 2015-2021 | |
| 21 | José López | 24 | 2032-2035 | |
| 21 | Mathieu Neri | 24 | 2024-2033 | |
| 21 | Lester Sullivan | 24 | 2018-2020 | |
| 29 | Jeff Cox | 23 | 2018-2021 | |
| 29 | Mike Foltynewicz | 23 | 2026-2028 | |
| 29 | Ken French# | 23 | 2034-2038 | |
| 29 | Kazuchika Okada# | 23 | 2034-2036 | |
| 29 | Titus Parson | 23 | 2023-2027 | |
| 34 | Fernando Elías# | 22 | 2031-2034 | |
| 34 | Hirokichi Kichida | 22 | 2018-2020 | |
| 34 | Hercules Mata'afa# | 22 | 2031-2035 | |
| 34 | Doruk Oyan | 22 | 2020-2022 | |
| 38 | Jamey Crockett | 21 | 2030-2033 | |
| 38 | Christian Harris | 21 | 2025-2029 | |
| 38 | Maxime Janssens# | 21 | 2026-2027 | |
| 38 | Ollie McDaniell# | 21 | 2031-2032 | |
| 38 | Adam Oldenkamp | 21 | 2030-2033 | |
| 38 | Luis Ortíz | 21 | 2020-2026 | |
| 38 | Joseph Reed | 21 | 2018-2023 | |
| 45 | Darius Baxa | 20 | 2027-2028 | |
| 45 | Roberto Cabrera# | 20 | 2037-2038 | |
| 45 | Jorge Carrión | 20 | 2020-2025 | |
| 45 | Joel Farrell# | 20 | 2030-2031 | |
| 45 | Tom Gaillard | 20 | 2015-2018 | |
| 45 | Hong-bin Hua# | 20 | 2033-2034 | |
| 45 | Teddy Jones | 20 | 2020-2022 | |
| 45 | Kyle McPherson | 20 | 2018-2023 | |
| 45 | Carlos Méndez | 20 | 2019-2020 | |
| 45 | Phil Miller | 20 | 2026-2028 | |
| 55 | Art Adams | 19 | 2017-2019 | |
| 55 | Benjamin Brouwer | 19 | 2021-2022 | |
| 55 | José Colón# | 19 | 2034-2038 | |
| 55 | Javier Mena | 19 | 2026-2032 | |
| 55 | Ramón Ocegueda | 19 | 2029-2032 | |
| 55 | Doppo Omikado# | 19 | 2029-2032 | |
| 55 | Dave Seals# | 19 | 2025-2028 | |
| 55 | Vernon Turner | 19 | 2023-2027 | |
| 55 | António Uribe | 19 | 2018-2021 | |
| 55 | Loeck Visser | 19 | 2023-2027 | |
| 65 | José Cotilla# | 18 | 2029-2030 | |
| 65 | Ralph DePalma# | 18 | 2033-2035 | |
| 65 | Craig Fitzgerald# | 18 | 2034-2035 | |
| 65 | Brandeis Göller | 18 | 2022-2023 | |
| 65 | Daniel Lavalley# | 18 | 2030-2033 | |
| 65 | Mack MacDonald | 18 | 2026-2028 | |
| 65 | Carl MacPherson# | 18 | 2034-2036 | |
| 65 | Rich McLean# | 18 | 2029-2034 | |
| 65 | Francisco Mora | 18 | 2018-2020 | |
| 65 | Félix Rodríguez | 18 | 2019-2020 | |
| 65 | Damien Scudder | 18 | 2024-2026 | |
| 65 | Curt Tate | 18 | 2023-2024 | |
| 65 | Blair Wright# | 18 | 2031-2032 | |
| 78 | Antoine Ayuso | 17 | 2027-2031 | |
| 78 | António Bruno | 17 | 2024-2026 | |
| 78 | Steve Bryan | 17 | 2016-2024 | |
| 78 | Ryan Dull# | 17 | 2028-2031 | |
| 78 | Derek Fisher | 17 | 2035-2037 | |
| 78 | Carlos González# | 17 | 2036-2038 | |
| 78 | Ryunosuke Kurota# | 17 | 2031-2032 | |
| 78 | Kevin Maughan# | 17 | 2033-2036 | |
| 78 | Ralph McKinney | 17 | 2015-2018 | |
| 78 | Alberto Ortíz | 17 | 2030-2034 | |
| 78 | Eugenio Pińeiro# | 17 | 2031-2032 | |
| 78 | Gilberto Ramírez | 17 | 2022-2031 | |
| 78 | Roger Rodenburg# | 17 | 2033-2034 | |
| 78 | Carlos Salcido# | 17 | 2031-2032 | |
| 78 | Rob Silva# | 17 | 2025-2026 | |
| 78 | Alex Simmons | 17 | 2020-2021 | |
| 78 | Dave Turner | 17 | 2024-2026 | |
| 78 | Winston Wenham | 17 | 2030-2033 | |
| 78 | Russ Wood | 17 | 2017-2031 | |
| 78 | Won-min Yi | 17 | 2031-2036 | |
| 98 | Benedicto Castellon | 16 | 2030-2035 | |
| 98 | Jack King | 16 | 2025-2026 | |
| 98 | Ramón Leyva | 16 | 2016-2019 |
