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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 | Carl MacPherson# | 35 | 2031-2035 | |
| 3 | Joe Holland# | 29 | 2034-2036 | |
| 4 | Pedro Adame | 28 | 2026-2028 | |
| 5 | Zach Pinyerrel# | 27 | 2029-2034 | |
| 5 | Cristóbal Román# | 27 | 2032-2034 | |
| 5 | Edward Scarborough | 27 | 2026-2029 | |
| 8 | Erik Illescas | 26 | 2031-2035 | |
| 8 | Santtu Öunap# | 26 | 2031-2036 | |
| 10 | Loren Berdine | 25 | 2027-2029 | |
| 10 | Bob Browning# | 25 | 2023-2025 | |
| 10 | Gabriel Escobar# | 25 | 2022-2025 | |
| 10 | Felipe Pereira | 25 | 2024-2027 | |
| 14 | Kevin Beckman# | 24 | 2032-2035 | |
| 14 | Morihiro Sai | 24 | 2025-2027 | |
| 14 | Rusty Swanson# | 24 | 2023-2025 | |
| 17 | Kent Horton# | 23 | 2030-2032 | |
| 17 | Cisco Pérez# | 23 | 2029-2030 | |
| 17 | Alejandro Ramos | 23 | 2021-2025 | |
| 17 | Tony Torres# | 23 | 2031-2032 | |
| 21 | Gonzalo Montés | 22 | 2022-2026 | |
| 21 | Nick Richie | 22 | 2022-2024 | |
| 23 | Francisco Burgos | 21 | 2025-2028 | |
| 23 | José López | 21 | 2026-2028 | |
| 25 | Benjamin Busto# | 20 | 2025-2027 | |
| 25 | Harrison Dunning# | 20 | 2030-2031 | |
| 25 | Justin Flynn | 20 | 2029-2030 | |
| 25 | Kewiki Pua | 20 | 2029-2030 | |
| 25 | Turner Shamburger# | 20 | 2030-2033 | |
| 30 | Phillip Donoghue# | 19 | 2029-2033 | |
| 30 | Evan Groenevelt# | 19 | 2031-2035 | |
| 30 | Song-saeng Kim | 19 | 2021-2024 | |
| 30 | António Marés# | 19 | 2021-2022 | |
| 30 | Ismael Riddles# | 19 | 2033-2036 | |
| 30 | José Santiago# | 19 | 2024-2027 | |
| 30 | Alberto Solís | 19 | 2025-2027 | |
| 30 | Josef Strolz | 19 | 2023-2025 | |
| 38 | Darius Baxa | 18 | 2025-2026 | |
| 38 | Jim Davis | 18 | 2021-2025 | |
| 38 | Al Gagne# | 18 | 2034-2035 | |
| 38 | Ramiro García | 18 | 2022-2024 | |
| 38 | Chae-seong Kim | 18 | 2021-2022 | |
| 38 | Donnie Rawling# | 18 | 2034-2036 | |
| 38 | Ánibal Rivera | 18 | 2020-2022 | |
| 38 | Jon Shirley | 18 | 2023-2024 | |
| 46 | Guus Danen# | 17 | 2034-2036 | |
| 46 | Andy Fallon# | 17 | 2029-2030 | |
| 46 | Van Lapointe# | 17 | 2031-2035 | |
| 46 | Ismael Lara | 17 | 2024-2027 | |
| 46 | Ed Molloy# | 17 | 2030-2033 | |
| 46 | James Neutron | 17 | 2024-2026 | |
| 46 | William Penn | 17 | 2032-2034 | |
| 46 | Osiris St. Brown | 17 | 2027-2028 | |
| 46 | Jorge Travieso# | 17 | 2028-2030 | |
| 55 | Ramón Cortéz | 16 | 2028-2032 | |
| 55 | António Fernández# | 16 | 2030-2032 | |
| 55 | Luis Hernández | 16 | 2025-2026 | |
| 55 | Kade Kinnamon | 16 | 2030-2032 | |
| 55 | Juan López | 16 | 2020-2022 | |
| 55 | António Muńóz# | 16 | 2026-2027 | |
| 55 | Mark Parker# | 16 | 2033-2034 | |
| 55 | Tony Solíz# | 16 | 2023-2024 | |
| 55 | Wilson Valenzuela# | 16 | 2031-2035 | |
| 64 | Wendell Baldwin# | 15 | 2034-2035 | |
| 64 | Don Bender | 15 | 2020-2021 | |
| 64 | Manuel Ceja | 15 | 2027-2028 | |
| 64 | Amando Codes# | 15 | 2030-2032 | |
| 64 | Hänsel Freeh | 15 | 2020-2021 | |
| 64 | NaNomi Lojore# | 15 | 2030-2030 | |
| 64 | Sjoerd Reynoud# | 15 | 2027-2029 | |
| 64 | Jon Schultz | 15 | 2021-2023 | |
| 64 | Marco Sledge | 15 | 2024-2029 | |
| 64 | Jack Tucker# | 15 | 2033-2034 | |
| 74 | Ryan Dull# | 14 | 2024-2028 | |
| 74 | Harold Elkins | 14 | 2020-2022 | |
| 74 | Ken French# | 14 | 2031-2034 | |
| 74 | Ángel Gardener# | 14 | 2031-2032 | |
| 74 | Tomás Gonzáles | 14 | 2020-2021 | |
| 74 | Valentyn Hochmiller# | 14 | 2029-2032 | |
| 74 | John Kraan# | 14 | 2030-2033 | |
| 74 | Enrique Madrid | 14 | 2021-2023 | |
| 74 | Jorge Moreno# | 14 | 2031-2034 | |
| 74 | Roger Murdock | 14 | 2026-2027 | |
| 74 | Adrian Neumann | 14 | 2020-2021 | |
| 74 | Pang Qin# | 14 | 2026-2027 | |
| 74 | Salvador Sagastizabal# | 14 | 2030-2033 | |
| 74 | Chet Saks# | 14 | 2027-2028 | |
| 74 | Shunen Takahashi | 14 | 2021-2021 | |
| 89 | Chiel Abspoel | 13 | 2025-2026 | |
| 89 | António Andrade | 13 | 2025-2026 | |
| 89 | Mark Bell | 13 | 2020-2022 | |
| 89 | John Bennett# | 13 | 2033-2034 | |
| 89 | Luis Bustamante | 13 | 2027-2029 | |
| 89 | Víctor Deleón# | 13 | 2034-2035 | |
| 89 | Ron Fernández# | 13 | 2032-2032 | |
| 89 | Natalino Golaio# | 13 | 2020-2021 | |
| 89 | Joe Griffin | 13 | 2020-2021 | |
| 89 | Sam Groves | 13 | 2024-2024 | |
| 89 | Santos Guzowski | 13 | 2024-2025 | |
| 89 | Heyg Lamper | 13 | 2025-2027 |
