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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# | 30 | 2031-2034 | |
| 3 | Pedro Adame# | 28 | 2026-2028 | |
| 4 | Zach Pinyerrel# | 27 | 2029-2034 | |
| 4 | Cristóbal Román# | 27 | 2032-2034 | |
| 4 | Edward Scarborough# | 27 | 2026-2029 | |
| 7 | Loren Berdine# | 25 | 2027-2029 | |
| 7 | Bob Browning# | 25 | 2023-2025 | |
| 7 | Gabriel Escobar# | 25 | 2022-2025 | |
| 7 | Felipe Pereira# | 25 | 2024-2027 | |
| 11 | Morihiro Sai | 24 | 2025-2027 | |
| 11 | Rusty Swanson# | 24 | 2023-2025 | |
| 13 | Kent Horton# | 23 | 2030-2032 | |
| 13 | Cisco Pérez# | 23 | 2029-2030 | |
| 13 | Alejandro Ramos | 23 | 2021-2025 | |
| 13 | Tony Torres# | 23 | 2031-2032 | |
| 17 | Gonzalo Montés | 22 | 2022-2026 | |
| 17 | Nick Richie | 22 | 2022-2024 | |
| 19 | Francisco Burgos# | 21 | 2025-2028 | |
| 19 | Erik Illescas# | 21 | 2031-2034 | |
| 19 | José López# | 21 | 2026-2028 | |
| 22 | Benjamin Busto# | 20 | 2025-2027 | |
| 22 | Harrison Dunning# | 20 | 2030-2031 | |
| 22 | Justin Flynn | 20 | 2029-2030 | |
| 22 | Kewiki Pua | 20 | 2029-2030 | |
| 22 | Turner Shamburger# | 20 | 2030-2033 | |
| 27 | Phillip Donoghue# | 19 | 2029-2033 | |
| 27 | Evan Groenevelt# | 19 | 2031-2034 | |
| 27 | Song-saeng Kim# | 19 | 2021-2024 | |
| 27 | António Marés# | 19 | 2021-2022 | |
| 27 | José Santiago# | 19 | 2024-2027 | |
| 27 | Alberto Solís# | 19 | 2025-2027 | |
| 27 | Josef Strolz | 19 | 2023-2025 | |
| 34 | Darius Baxa# | 18 | 2025-2026 | |
| 34 | Jim Davis | 18 | 2021-2025 | |
| 34 | Ramiro García | 18 | 2022-2024 | |
| 34 | Chae-seong Kim# | 18 | 2021-2022 | |
| 34 | Ánibal Rivera | 18 | 2020-2022 | |
| 34 | Jon Shirley | 18 | 2023-2024 | |
| 40 | Kevin Beckman# | 17 | 2032-2034 | |
| 40 | Andy Fallon# | 17 | 2029-2030 | |
| 40 | Ismael Lara# | 17 | 2024-2027 | |
| 40 | Ed Molloy# | 17 | 2030-2033 | |
| 40 | James Neutron# | 17 | 2024-2026 | |
| 40 | William Penn# | 17 | 2032-2034 | |
| 40 | Osiris St. Brown# | 17 | 2027-2028 | |
| 40 | Jorge Travieso# | 17 | 2028-2030 | |
| 48 | Ramón Cortéz# | 16 | 2028-2032 | |
| 48 | António Fernández# | 16 | 2030-2032 | |
| 48 | Luis Hernández | 16 | 2025-2026 | |
| 48 | Kade Kinnamon# | 16 | 2030-2032 | |
| 48 | Juan López# | 16 | 2020-2022 | |
| 48 | António Muńóz# | 16 | 2026-2027 | |
| 48 | Mark Parker# | 16 | 2033-2034 | |
| 48 | Tony Solíz# | 16 | 2023-2024 | |
| 56 | Don Bender | 15 | 2020-2021 | |
| 56 | Manuel Ceja# | 15 | 2027-2028 | |
| 56 | Amando Codes# | 15 | 2030-2032 | |
| 56 | Hänsel Freeh | 15 | 2020-2021 | |
| 56 | Van Lapointe# | 15 | 2031-2033 | |
| 56 | NaNomi Lojore# | 15 | 2030-2030 | |
| 56 | Sjoerd Reynoud# | 15 | 2027-2029 | |
| 56 | Ismael Riddles# | 15 | 2033-2034 | |
| 56 | Jon Schultz | 15 | 2021-2023 | |
| 56 | Marco Sledge# | 15 | 2024-2029 | |
| 56 | Jack Tucker# | 15 | 2033-2034 | |
| 67 | Ryan Dull# | 14 | 2024-2028 | |
| 67 | Harold Elkins | 14 | 2020-2022 | |
| 67 | Ken French# | 14 | 2031-2034 | |
| 67 | Ángel Gardener# | 14 | 2031-2032 | |
| 67 | Tomás Gonzáles | 14 | 2020-2021 | |
| 67 | Valentyn Hochmiller# | 14 | 2029-2032 | |
| 67 | John Kraan# | 14 | 2030-2033 | |
| 67 | Enrique Madrid | 14 | 2021-2023 | |
| 67 | Jorge Moreno# | 14 | 2031-2034 | |
| 67 | Roger Murdock | 14 | 2026-2027 | |
| 67 | Adrian Neumann# | 14 | 2020-2021 | |
| 67 | Pang Qin# | 14 | 2026-2027 | |
| 67 | Salvador Sagastizabal# | 14 | 2030-2033 | |
| 67 | Chet Saks# | 14 | 2027-2028 | |
| 67 | Shunen Takahashi# | 14 | 2021-2021 | |
| 82 | Chiel Abspoel# | 13 | 2025-2026 | |
| 82 | António Andrade# | 13 | 2025-2026 | |
| 82 | Mark Bell# | 13 | 2020-2022 | |
| 82 | John Bennett# | 13 | 2033-2034 | |
| 82 | Luis Bustamante# | 13 | 2027-2029 | |
| 82 | Ron Fernández# | 13 | 2032-2032 | |
| 82 | Natalino Golaio# | 13 | 2020-2021 | |
| 82 | Joe Griffin | 13 | 2020-2021 | |
| 82 | Sam Groves# | 13 | 2024-2024 | |
| 82 | Santos Guzowski | 13 | 2024-2025 | |
| 82 | Joe Holland# | 13 | 2034-2034 | |
| 82 | Heyg Lamper | 13 | 2025-2027 | |
| 82 | Jeff Lee | 13 | 2020-2020 | |
| 82 | Claudio Mateo# | 13 | 2027-2030 | |
| 82 | Manuel Montés | 13 | 2023-2026 | |
| 82 | Rafael Narváez# | 13 | 2030-2033 | |
| 82 | Santtu Öunap# | 13 | 2031-2034 | |
| 82 | Fernando Ramírez# | 13 | 2024-2024 | |
| 82 | David Rowlingson# | 13 | 2030-2033 |
