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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Josh Bailey | 31 | 2026-2030 | |
| 2 | Mike Bliss | 20 | 2029-2032 | |
| 3 | Eric Capers# | 17 | 2028-2030 | |
| 4 | Chris Cruse | 16 | 2030-2033 | |
| 4 | Sam Lawrence | 16 | 2029-2031 | |
| 4 | Sebastian Perrone | 16 | 2020-2022 | |
| 7 | Sam Hendershot | 15 | 2025-2027 | |
| 7 | Mike Mendoza | 15 | 2030-2032 | |
| 9 | Ruben Alvarado# | 14 | 2035-2036 | |
| 9 | Tony Calderon | 14 | 2025-2029 | |
| 9 | Jorge de la Rosa | 14 | 2028-2032 | |
| 9 | Jake Layton# | 14 | 2032-2036 | |
| 9 | Steve Marcelletti# | 14 | 2035-2036 | |
| 9 | Jonathan Woods | 14 | 2023-2027 | |
| 15 | Pat Biddle# | 13 | 2031-2035 | |
| 15 | William Gonzalez | 13 | 2020-2024 | |
| 15 | Dave Hanegan# | 13 | 2030-2033 | |
| 15 | Josh Holst | 13 | 2026-2031 | |
| 15 | Chris Huerta | 13 | 2021-2025 | |
| 15 | Bobby MacLeod | 13 | 2030-2031 | |
| 15 | Juan Montano# | 13 | 2030-2032 | |
| 15 | Ben Shoemaker# | 13 | 2033-2036 | |
| 15 | Gabe Skane# | 13 | 2033-2036 | |
| 15 | Dan Wasson | 13 | 2025-2028 | |
| 15 | Phil Wilson# | 13 | 2029-2033 | |
| 26 | Josh Anderson# | 12 | 2035-2036 | |
| 26 | Mike Bevil# | 12 | 2030-2033 | |
| 26 | Zach Daniels | 12 | 2018-2022 | |
| 26 | Garrett Davila | 12 | 2016-2020 | |
| 26 | Ivran Engel# | 12 | 2031-2034 | |
| 26 | Eric Hill# | 12 | 2030-2033 | |
| 26 | Kevin Kelley | 12 | 2029-2031 | |
| 26 | Dan Miller | 12 | 2020-2023 | |
| 26 | Phil Pakpahan | 12 | 2020-2024 | |
| 26 | Jon Slack# | 12 | 2030-2034 | |
| 26 | Ronnie Swierkowski# | 12 | 2034-2036 | |
| 26 | Barnabé Varregosa | 12 | 2025-2028 | |
| 38 | Luis Avina | 11 | 2027-2031 | |
| 38 | Rick Behenna | 11 | 1978-1979 | |
| 38 | Bill Bell | 11 | 1952-1952 | |
| 38 | Josh Burris | 11 | 2012-2014 | |
| 38 | Jose Campos# | 11 | 2031-2033 | |
| 38 | Zach D'Ambrosio# | 11 | 2033-2036 | |
| 38 | D.J. Darden | 11 | 2027-2028 | |
| 38 | Donys Garcia | 11 | 2020-2022 | |
| 38 | JJ Goss# | 11 | 2022-2023 | |
| 38 | Jaiden Hall# | 11 | 2034-2036 | |
| 38 | Tim Shibuya | 11 | 2011-2013 | |
| 38 | Steve Sigler# | 11 | 2033-2036 | |
| 38 | Dan Spires | 11 | 2028-2031 | |
| 38 | Pete Tucker# | 11 | 2033-2035 | |
| 38 | Randy Vasquez | 11 | 2019-2021 | |
| 53 | Jeremy Bass# | 10 | 2034-2036 | |
| 53 | Steve Bowen | 10 | 2022-2024 | |
| 53 | Tommie Chapin | 10 | 2021-2025 | |
| 53 | Dave D'Agostin | 10 | 2025-2028 | |
| 53 | Mike Dillard | 10 | 2026-2029 | |
| 53 | Chad Dobis | 10 | 2028-2031 | |
| 53 | Tim Herder# | 10 | 2032-2033 | |
| 53 | Dailyn Martinez | 10 | 2013-2014 | |
| 53 | Marcelo Martinez | 10 | 2018-2018 | |
| 53 | Jon Milioto | 10 | 2029-2030 | |
| 53 | Tyler Mortensen | 10 | 2021-2024 | |
| 53 | Omar Mosquera | 10 | 2025-2027 | |
| 53 | Jose Olague | 10 | 2020-2021 | |
| 53 | Jim Orr | 10 | 2026-2029 | |
| 53 | Manny Paramo# | 10 | 2023-2027 | |
| 53 | Alex Renteria | 10 | 2023-2027 | |
| 53 | Luis Rijo | 10 | 2018-2018 | |
| 53 | Levi Romero | 10 | 2003-2004 | |
| 53 | Dan Shearing | 10 | 2026-2028 | |
| 53 | Ernesto Silva | 10 | 2011-2013 | |
| 53 | Chad Sosnowski# | 10 | 2026-2027 | |
| 53 | Willy Taveras | 10 | 2018-2018 | |
| 53 | Jim Waldroup | 10 | 2023-2026 | |
| 53 | Chris Warrens | 10 | 2030-2033 | |
| 53 | Marlin Willis | 10 | 2018-2020 | |
| 78 | Josh Adams | 9 | 2022-2025 | |
| 78 | Jaden Barksdale | 9 | 2029-2031 | |
| 78 | Olivier Basabe | 9 | 2005-2006 | |
| 78 | Don Beaupre# | 9 | 2032-2036 | |
| 78 | David Bromberg | 9 | 2007-2007 | |
| 78 | Rusty Capobianco | 9 | 2022-2023 | |
| 78 | Steve DiMora | 9 | 2025-2025 | |
| 78 | William Figueroa | 9 | 2022-2023 | |
| 78 | Chris Flexen | 9 | 2012-2013 | |
| 78 | Shane Greenwood# | 9 | 2029-2031 | |
| 78 | Chris Griffin | 9 | 2023-2026 | |
| 78 | J.C. Gutierrez | 9 | 2003-2004 | |
| 78 | Aaron Harang | 9 | 1999-1999 | |
| 78 | Jaret Hellinger | 9 | 2016-2020 | |
| 78 | Ruben Lara# | 9 | 2032-2033 | |
| 78 | Sean Locke | 9 | 2028-2031 | |
| 78 | Steve Maddox | 9 | 2027-2028 | |
| 78 | Dilmer Mejia | 9 | 2017-2018 | |
| 78 | Luis Mendoza | 9 | 2029-2031 | |
| 78 | Chris Mongrain | 9 | 2021-2023 | |
| 78 | Edwin Ocanas | 9 | 2030-2031 | |
| 78 | Eric Parker# | 9 | 2029-2033 | |
| 78 | Josh Peterson# | 9 | 2027-2028 |
