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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 | Umebayashi Naofumi# | 24 | 2034-2038 | |
| 14 | Morihiro Sai | 24 | 2025-2027 | |
| 14 | Rusty Swanson | 24 | 2023-2025 | |
| 18 | Kent Horton# | 23 | 2030-2032 | |
| 18 | Cisco Pérez# | 23 | 2029-2030 | |
| 18 | Alejandro Ramos | 23 | 2021-2025 | |
| 18 | Tony Torres# | 23 | 2031-2032 | |
| 22 | Gonzalo Montés | 22 | 2022-2026 | |
| 22 | Donnie Rawling# | 22 | 2034-2037 | |
| 22 | Nick Richie | 22 | 2022-2024 | |
| 25 | Francisco Burgos | 21 | 2025-2028 | |
| 25 | Dave Hamilton# | 21 | 2037-2040 | |
| 25 | José López | 21 | 2026-2028 | |
| 28 | Benjamin Busto | 20 | 2025-2027 | |
| 28 | Harrison Dunning | 20 | 2030-2031 | |
| 28 | Justin Flynn | 20 | 2029-2030 | |
| 28 | Kewiki Pua | 20 | 2029-2030 | |
| 28 | Turner Shamburger# | 20 | 2030-2033 | |
| 33 | Phillip Donoghue | 19 | 2029-2033 | |
| 33 | Evan Groenevelt# | 19 | 2031-2035 | |
| 33 | Song-saeng Kim | 19 | 2021-2024 | |
| 33 | António Marés | 19 | 2021-2022 | |
| 33 | Ismael Riddles# | 19 | 2033-2036 | |
| 33 | José Santiago | 19 | 2024-2027 | |
| 33 | Alberto Solís | 19 | 2025-2027 | |
| 33 | Josef Strolz | 19 | 2023-2025 | |
| 41 | Darius Baxa | 18 | 2025-2026 | |
| 41 | Jim Davis | 18 | 2021-2025 | |
| 41 | John Fleming# | 18 | 2038-2039 | |
| 41 | Ramón Flores# | 18 | 2035-2037 | |
| 41 | Al Gagne | 18 | 2034-2035 | |
| 41 | Ramiro García | 18 | 2022-2024 | |
| 41 | Chae-seong Kim | 18 | 2021-2022 | |
| 41 | Ánibal Rivera | 18 | 2020-2022 | |
| 41 | Jon Shirley | 18 | 2023-2024 | |
| 41 | Paul Workman# | 18 | 2035-2037 | |
| 51 | Guus Danen# | 17 | 2034-2036 | |
| 51 | Andy Fallon | 17 | 2029-2030 | |
| 51 | Van Lapointe# | 17 | 2031-2035 | |
| 51 | Ismael Lara | 17 | 2024-2027 | |
| 51 | Ed Molloy | 17 | 2030-2033 | |
| 51 | James Neutron | 17 | 2024-2026 | |
| 51 | Miguel Núńez# | 17 | 2037-2040 | |
| 51 | William Penn | 17 | 2032-2034 | |
| 51 | Jesús Ríos# | 17 | 2038-2040 | |
| 51 | Osiris St. Brown | 17 | 2027-2028 | |
| 51 | Jorge Travieso | 17 | 2028-2030 | |
| 62 | Ramón Cortéz | 16 | 2028-2032 | |
| 62 | António Fernández | 16 | 2030-2032 | |
| 62 | Shawn Hanna# | 16 | 2039-2040 | |
| 62 | Luis Hernández | 16 | 2025-2026 | |
| 62 | Kade Kinnamon | 16 | 2030-2032 | |
| 62 | Juan López | 16 | 2020-2022 | |
| 62 | António Muńóz# | 16 | 2026-2027 | |
| 62 | Mark Parker | 16 | 2033-2034 | |
| 62 | Carlos Simon# | 16 | 2034-2037 | |
| 62 | Tony Solíz | 16 | 2023-2024 | |
| 62 | Wilson Valenzuela# | 16 | 2031-2035 | |
| 62 | Steve Young# | 16 | 2038-2040 | |
| 74 | Wendell Baldwin | 15 | 2034-2035 | |
| 74 | Don Bender | 15 | 2020-2021 | |
| 74 | Manuel Ceja | 15 | 2027-2028 | |
| 74 | Amando Codes# | 15 | 2030-2032 | |
| 74 | Hänsel Freeh | 15 | 2020-2021 | |
| 74 | NaNomi Lojore# | 15 | 2030-2030 | |
| 74 | Don Murray# | 15 | 2038-2039 | |
| 74 | Sjoerd Reynoud# | 15 | 2027-2029 | |
| 74 | Jon Schultz | 15 | 2021-2023 | |
| 74 | Marco Sledge | 15 | 2024-2029 | |
| 74 | Mark Smith# | 15 | 2035-2037 | |
| 74 | Jack Tucker | 15 | 2033-2034 | |
| 86 | Ed Alexander# | 14 | 2037-2039 | |
| 86 | Ryan Dull | 14 | 2024-2028 | |
| 86 | Harold Elkins | 14 | 2020-2022 | |
| 86 | Ken French# | 14 | 2031-2034 | |
| 86 | Ángel Gardener | 14 | 2031-2032 | |
| 86 | Tomás Gonzáles | 14 | 2020-2021 | |
| 86 | Valentyn Hochmiller# | 14 | 2029-2032 | |
| 86 | Rick Hubbard# | 14 | 2037-2039 | |
| 86 | Javier Iturburua# | 14 | 2037-2040 | |
| 86 | John Kraan# | 14 | 2030-2033 | |
| 86 | Enrique Madrid | 14 | 2021-2023 | |
| 86 | Jorge Moreno# | 14 | 2031-2034 | |
| 86 | Roger Murdock | 14 | 2026-2027 | |
| 86 | Adrian Neumann | 14 | 2020-2021 | |
| 86 | Pang Qin# | 14 | 2026-2027 |
