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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Casey Painter | 72 | 2019-2028 | |
| 2 | Kil-sung Kim# | 70 | 2033-2041 | |
| 3 | Rodrigo Rosado# | 63 | 2034-2041 | |
| 4 | Fred Burdett | 60 | 2035-2040 | |
| 5 | Jeremiah Andrews | 50 | 2033-2036 | |
| 6 | Justin Garner | 49 | 2029-2032 | |
| 7 | Jorge Herrera | 47 | 2033-2036 | |
| 8 | Brian Ashby | 46 | 2018-2024 | |
| 8 | Isaac Daniels# | 46 | 2037-2040 | |
| 10 | Paul Gideon | 45 | 2034-2040 | |
| 11 | Mike Hood | 44 | 2025-2033 | |
| 11 | Greg Rawson | 44 | 2022-2030 | |
| 11 | Victor Rodriguez | 44 | 2018-2024 | |
| 14 | Nick Harris | 43 | 2027-2032 | |
| 14 | Seika Nikaido | 43 | 2018-2025 | |
| 16 | Quadir Bryant | 42 | 2019-2022 | |
| 16 | Adrian Mowery | 42 | 2021-2028 | |
| 18 | Steve Runk# | 41 | 2037-2039 | |
| 19 | Omar Chavez# | 40 | 2031-2040 | |
| 19 | Ben Wiseman# | 40 | 2035-2039 | |
| 21 | Bryant Bryan# | 39 | 2035-2037 | |
| 21 | Phil Keohane | 39 | 2027-2033 | |
| 21 | Jim Neely | 39 | 2031-2035 | |
| 21 | Nelson Ramos | 39 | 2028-2032 | |
| 21 | Mike Stout | 39 | 2036-2039 | |
| 26 | Marcos Adames | 38 | 2022-2031 | |
| 26 | Jayden Baker# | 38 | 2037-2041 | |
| 26 | Al Brownell | 38 | 2018-2026 | |
| 26 | Travis Schmidt | 38 | 2018-2024 | |
| 30 | Blake Asplin# | 37 | 2039-2041 | |
| 30 | Pedro Moreno# | 37 | 2031-2035 | |
| 30 | Sean Nagy | 37 | 2020-2028 | |
| 33 | Chris Anderson# | 36 | 2025-2027 | |
| 33 | Brian Hanley | 36 | 2026-2033 | |
| 33 | Evan Tirrell# | 36 | 2030-2035 | |
| 36 | Pyotr Upyrin | 35 | 2025-2032 | |
| 37 | Jerry Klein | 34 | 2018-2022 | |
| 38 | Kyle Chitwood | 33 | 2020-2032 | |
| 38 | Paul Doyle | 33 | 2029-2031 | |
| 38 | Miguel Leon | 33 | 2031-2035 | |
| 38 | Hugo Torres | 33 | 2025-2032 | |
| 38 | Dave Wishart | 33 | 2029-2037 | |
| 43 | José Batista# | 32 | 2033-2036 | |
| 43 | Shane Berry | 32 | 2034-2039 | |
| 43 | Gabriel Manzueta | 32 | 2026-2030 | |
| 43 | Tony Sanders# | 32 | 2036-2041 | |
| 43 | Alex Zuniga | 32 | 2028-2032 | |
| 48 | Ira Aguilar# | 31 | 2028-2039 | |
| 48 | Jeff Aguilar | 31 | 2037-2039 | |
| 48 | Ben Doutrich | 31 | 2019-2023 | |
| 48 | Ruben Estrada | 31 | 2028-2034 | |
| 48 | Danny Fernandez | 31 | 2019-2023 | |
| 48 | Ange Riou | 31 | 2018-2021 | |
| 54 | Alex Burd# | 30 | 2036-2039 | |
| 54 | Jordan Cheyne | 30 | 2026-2030 | |
| 54 | Omar Garcia# | 30 | 2031-2035 | |
| 54 | Ruben Gutierrez | 30 | 2020-2023 | |
| 54 | Jose Moran | 30 | 2036-2039 | |
| 54 | Phil Morris | 30 | 2020-2024 | |
| 54 | Jesus Valdemar# | 30 | 2036-2041 | |
| 54 | Matt Walter | 30 | 2035-2037 | |
| 62 | Bobby Giron | 29 | 2028-2031 | |
| 62 | Terrell Hargrove# | 29 | 2034-2041 | |
| 62 | Lukyan Jakushin# | 29 | 2027-2039 | |
| 62 | Donald Williams | 29 | 2022-2025 | |
| 66 | Nick Boyle# | 28 | 2036-2041 | |
| 66 | Hector Fernandez# | 28 | 2039-2041 | |
| 66 | Andrew O'Donnell# | 28 | 2033-2041 | |
| 66 | Adam Venable | 28 | 2039-2041 | |
| 70 | Shane Baker# | 27 | 2036-2041 | |
| 70 | Chris Barber | 27 | 2021-2026 | |
| 70 | Richard Chenault | 27 | 2029-2034 | |
| 70 | Jose Davila | 27 | 2021-2031 | |
| 70 | Justin Longcoy | 27 | 2034-2038 | |
| 75 | Dave Adams# | 26 | 2026-2029 | |
| 75 | Steve Adams | 26 | 2026-2032 | |
| 75 | Garrett Douglas# | 26 | 2028-2030 | |
| 75 | Ryan Duffield | 26 | 2022-2024 | |
| 75 | Lawrence Dupree | 26 | 2018-2021 | |
| 75 | Markus Gelsomino | 26 | 2033-2037 | |
| 75 | Tyler Hamm | 26 | 2027-2032 | |
| 75 | Paul Hoekstra | 26 | 2036-2038 | |
| 75 | Aaron Justice | 26 | 2024-2028 | |
| 75 | Alex Perez# | 26 | 2035-2039 | |
| 75 | Javier Saraiva | 26 | 2022-2024 | |
| 75 | Cole Shapiro | 26 | 2024-2032 | |
| 87 | Brent Acret# | 25 | 2038-2040 | |
| 87 | Ray Atkinson# | 25 | 2035-2041 | |
| 87 | Robby Carmona | 25 | 2021-2024 | |
| 87 | Félix Chamio | 25 | 2028-2032 | |
| 87 | Angel de Jesus | 25 | 2028-2034 | |
| 87 | Josh Duclos | 25 | 2033-2036 | |
| 87 | Arturo Espejo# | 25 | 2038-2041 | |
| 87 | Chuck Haynes | 25 | 2018-2022 | |
| 87 | Noah Hoffman# | 25 | 2028-2031 | |
| 87 | Angelo Poblano | 25 | 2037-2039 | |
| 87 | Chris Robinson | 25 | 2018-2021 | |
| 87 | Leonardo Sanchez# | 25 | 2037-2038 | |
| 87 | Jeff Seier | 25 | 2024-2027 | |
| 87 | Miguel Solis | 25 | 2023-2025 |
