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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 | Steve Baker# | 27 | 2040-2043 | |
| 5 | Zach Pinyerrel | 27 | 2029-2034 | |
| 5 | Cristóbal Román | 27 | 2032-2034 | |
| 5 | Edward Scarborough | 27 | 2026-2029 | |
| 9 | Erik Illescas | 26 | 2031-2035 | |
| 9 | Santtu Öunap | 26 | 2031-2036 | |
| 11 | Loren Berdine | 25 | 2027-2029 | |
| 11 | Bob Browning | 25 | 2023-2025 | |
| 11 | Gabriel Escobar | 25 | 2022-2025 | |
| 11 | Felipe Pereira | 25 | 2024-2027 | |
| 15 | Kevin Beckman | 24 | 2032-2035 | |
| 15 | Umebayashi Naofumi | 24 | 2034-2038 | |
| 15 | Morihiro Sai | 24 | 2025-2027 | |
| 15 | Rusty Swanson | 24 | 2023-2025 | |
| 19 | Kent Horton# | 23 | 2030-2032 | |
| 19 | Cisco Pérez | 23 | 2029-2030 | |
| 19 | Alejandro Ramos | 23 | 2021-2025 | |
| 19 | Tony Torres | 23 | 2031-2032 | |
| 23 | Gonzalo Montés | 22 | 2022-2026 | |
| 23 | Donnie Rawling | 22 | 2034-2037 | |
| 23 | Nick Richie | 22 | 2022-2024 | |
| 26 | Francisco Burgos | 21 | 2025-2028 | |
| 26 | Jeff Davis# | 21 | 2039-2041 | |
| 26 | Dave Hamilton# | 21 | 2037-2040 | |
| 26 | José López | 21 | 2026-2028 | |
| 30 | Benjamin Busto | 20 | 2025-2027 | |
| 30 | Harrison Dunning | 20 | 2030-2031 | |
| 30 | Justin Flynn | 20 | 2029-2030 | |
| 30 | Kewiki Pua | 20 | 2029-2030 | |
| 30 | Turner Shamburger# | 20 | 2030-2033 | |
| 30 | Dario Zorander# | 20 | 2040-2042 | |
| 36 | Phillip Donoghue | 19 | 2029-2033 | |
| 36 | Evan Groenevelt# | 19 | 2031-2035 | |
| 36 | Song-saeng Kim | 19 | 2021-2024 | |
| 36 | António Marés | 19 | 2021-2022 | |
| 36 | Rémy Moreau# | 19 | 2041-2043 | |
| 36 | Ismael Riddles# | 19 | 2033-2036 | |
| 36 | José Santiago | 19 | 2024-2027 | |
| 36 | Alberto Solís | 19 | 2025-2027 | |
| 36 | Josef Strolz | 19 | 2023-2025 | |
| 45 | Darius Baxa | 18 | 2025-2026 | |
| 45 | Jim Davis | 18 | 2021-2025 | |
| 45 | John Fleming# | 18 | 2038-2039 | |
| 45 | Ramón Flores# | 18 | 2035-2037 | |
| 45 | Al Gagne | 18 | 2034-2035 | |
| 45 | Ramiro García | 18 | 2022-2024 | |
| 45 | Chae-seong Kim | 18 | 2021-2022 | |
| 45 | Roberto Punyed# | 18 | 2039-2042 | |
| 45 | Ánibal Rivera | 18 | 2020-2022 | |
| 45 | Jon Shirley | 18 | 2023-2024 | |
| 45 | Javier Téllez# | 18 | 2039-2042 | |
| 45 | Paul Workman | 18 | 2035-2037 | |
| 57 | Jordon Glen Anderson# | 17 | 2039-2041 | |
| 57 | Guus Danen | 17 | 2034-2036 | |
| 57 | Andy Fallon | 17 | 2029-2030 | |
| 57 | Van Lapointe | 17 | 2031-2035 | |
| 57 | Ismael Lara | 17 | 2024-2027 | |
| 57 | Ed Molloy | 17 | 2030-2033 | |
| 57 | James Neutron | 17 | 2024-2026 | |
| 57 | Miguel Núńez# | 17 | 2037-2040 | |
| 57 | William Penn | 17 | 2032-2034 | |
| 57 | Jesús Ríos# | 17 | 2038-2040 | |
| 57 | Osiris St. Brown | 17 | 2027-2028 | |
| 57 | Jorge Travieso | 17 | 2028-2030 | |
| 69 | Ramón Cortéz | 16 | 2028-2032 | |
| 69 | António Fernández | 16 | 2030-2032 | |
| 69 | Shawn Hanna# | 16 | 2039-2040 | |
| 69 | Luis Hernández | 16 | 2025-2026 | |
| 69 | Kade Kinnamon | 16 | 2030-2032 | |
| 69 | Juan López | 16 | 2020-2022 | |
| 69 | António Muńóz | 16 | 2026-2027 | |
| 69 | Mark Parker | 16 | 2033-2034 | |
| 69 | Carlos Simon# | 16 | 2034-2037 | |
| 69 | Tony Solíz | 16 | 2023-2024 | |
| 69 | Wilson Valenzuela | 16 | 2031-2035 | |
| 69 | Steve Young# | 16 | 2038-2040 | |
| 81 | Wendell Baldwin | 15 | 2034-2035 | |
| 81 | Don Bender | 15 | 2020-2021 | |
| 81 | Leo Cassidy# | 15 | 2041-2042 | |
| 81 | Manuel Ceja | 15 | 2027-2028 | |
| 81 | Amando Codes# | 15 | 2030-2032 | |
| 81 | Hänsel Freeh | 15 | 2020-2021 | |
| 81 | NaNomi Lojore# | 15 | 2030-2030 | |
| 81 | Kevin Moran# | 15 | 2038-2041 | |
| 81 | Don Murray# | 15 | 2038-2039 | |
| 81 | Sjoerd Reynoud# | 15 | 2027-2029 | |
| 81 | Jon Schultz | 15 | 2021-2023 | |
| 81 | Marco Sledge | 15 | 2024-2029 | |
| 81 | Mark Smith | 15 | 2035-2037 | |
| 81 | Jack Tucker | 15 | 2033-2034 | |
| 95 | Ed Alexander# | 14 | 2037-2039 | |
| 95 | Otton Asmus# | 14 | 2040-2042 | |
| 95 | Roberto Días | 14 | 2040-2042 | |
| 95 | Ryan Dull | 14 | 2024-2028 | |
| 95 | Harold Elkins | 14 | 2020-2022 | |
| 95 | Ken French# | 14 | 2031-2034 |
