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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 | Donnie Rawling# | 22 | 2034-2037 | |
| 21 | Nick Richie | 22 | 2022-2024 | |
| 24 | Francisco Burgos | 21 | 2025-2028 | |
| 24 | José López | 21 | 2026-2028 | |
| 26 | Benjamin Busto# | 20 | 2025-2027 | |
| 26 | Harrison Dunning# | 20 | 2030-2031 | |
| 26 | Justin Flynn | 20 | 2029-2030 | |
| 26 | Kewiki Pua | 20 | 2029-2030 | |
| 26 | Turner Shamburger# | 20 | 2030-2033 | |
| 31 | Phillip Donoghue | 19 | 2029-2033 | |
| 31 | Evan Groenevelt# | 19 | 2031-2035 | |
| 31 | Song-saeng Kim | 19 | 2021-2024 | |
| 31 | António Marés# | 19 | 2021-2022 | |
| 31 | Ismael Riddles# | 19 | 2033-2036 | |
| 31 | José Santiago# | 19 | 2024-2027 | |
| 31 | Alberto Solís | 19 | 2025-2027 | |
| 31 | Josef Strolz | 19 | 2023-2025 | |
| 39 | Darius Baxa | 18 | 2025-2026 | |
| 39 | Jim Davis | 18 | 2021-2025 | |
| 39 | Ramón Flores# | 18 | 2035-2037 | |
| 39 | Al Gagne# | 18 | 2034-2035 | |
| 39 | Ramiro García | 18 | 2022-2024 | |
| 39 | Chae-seong Kim | 18 | 2021-2022 | |
| 39 | Ánibal Rivera | 18 | 2020-2022 | |
| 39 | Jon Shirley | 18 | 2023-2024 | |
| 39 | Paul Workman# | 18 | 2035-2037 | |
| 48 | Guus Danen# | 17 | 2034-2036 | |
| 48 | Andy Fallon# | 17 | 2029-2030 | |
| 48 | Van Lapointe# | 17 | 2031-2035 | |
| 48 | Ismael Lara | 17 | 2024-2027 | |
| 48 | Ed Molloy# | 17 | 2030-2033 | |
| 48 | James Neutron | 17 | 2024-2026 | |
| 48 | William Penn | 17 | 2032-2034 | |
| 48 | Osiris St. Brown | 17 | 2027-2028 | |
| 48 | Jorge Travieso | 17 | 2028-2030 | |
| 57 | Ramón Cortéz | 16 | 2028-2032 | |
| 57 | António Fernández# | 16 | 2030-2032 | |
| 57 | Luis Hernández | 16 | 2025-2026 | |
| 57 | Kade Kinnamon | 16 | 2030-2032 | |
| 57 | Juan López | 16 | 2020-2022 | |
| 57 | António Muńóz# | 16 | 2026-2027 | |
| 57 | Mark Parker# | 16 | 2033-2034 | |
| 57 | Carlos Simon# | 16 | 2034-2037 | |
| 57 | Tony Solíz# | 16 | 2023-2024 | |
| 57 | Wilson Valenzuela# | 16 | 2031-2035 | |
| 67 | Wendell Baldwin | 15 | 2034-2035 | |
| 67 | Don Bender | 15 | 2020-2021 | |
| 67 | Manuel Ceja | 15 | 2027-2028 | |
| 67 | Amando Codes# | 15 | 2030-2032 | |
| 67 | Hänsel Freeh | 15 | 2020-2021 | |
| 67 | NaNomi Lojore# | 15 | 2030-2030 | |
| 67 | Sjoerd Reynoud# | 15 | 2027-2029 | |
| 67 | Jon Schultz | 15 | 2021-2023 | |
| 67 | Marco Sledge | 15 | 2024-2029 | |
| 67 | Mark Smith# | 15 | 2035-2037 | |
| 67 | Jack Tucker# | 15 | 2033-2034 | |
| 78 | Ryan Dull# | 14 | 2024-2028 | |
| 78 | Harold Elkins | 14 | 2020-2022 | |
| 78 | Ken French# | 14 | 2031-2034 | |
| 78 | Ángel Gardener | 14 | 2031-2032 | |
| 78 | Tomás Gonzáles | 14 | 2020-2021 | |
| 78 | Valentyn Hochmiller# | 14 | 2029-2032 | |
| 78 | John Kraan# | 14 | 2030-2033 | |
| 78 | Enrique Madrid | 14 | 2021-2023 | |
| 78 | Jorge Moreno# | 14 | 2031-2034 | |
| 78 | Roger Murdock | 14 | 2026-2027 | |
| 78 | Adrian Neumann | 14 | 2020-2021 | |
| 78 | Pang Qin# | 14 | 2026-2027 | |
| 78 | Salvador Sagastizabal# | 14 | 2030-2033 | |
| 78 | Chet Saks# | 14 | 2027-2028 | |
| 78 | Shunen Takahashi | 14 | 2021-2021 | |
| 93 | Chiel Abspoel | 13 | 2025-2026 | |
| 93 | António Andrade | 13 | 2025-2026 | |
| 93 | Mark Bell | 13 | 2020-2022 | |
| 93 | John Bennett# | 13 | 2033-2034 | |
| 93 | Luis Bustamante | 13 | 2027-2029 | |
| 93 | Víctor Deleón# | 13 | 2034-2035 | |
| 93 | Ron Fernández# | 13 | 2032-2032 | |
| 93 | Natalino Golaio# | 13 | 2020-2021 |
