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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Tyler Baum | 55 | 2020-2025 | |
| 2 | Bob Ford | 38 | 2030-2031 | |
| 3 | Bobby Ay | 35 | 2020-2023 | |
| 4 | Bob Hass# | 32 | 2032-2035 | |
| 4 | Nate Sutton# | 32 | 2033-2035 | |
| 6 | Tony Saucedo# | 30 | 2031-2034 | |
| 7 | Jordan Sheffield | 29 | 2017-2022 | |
| 8 | Jon Michael Redding | 28 | 2010-2013 | |
| 8 | John Rooney | 28 | 2019-2022 | |
| 10 | Mike Schwartz | 27 | 2023-2025 | |
| 11 | Cole Bartlett | 26 | 2019-2023 | |
| 11 | Duany Gomez | 26 | 2021-2024 | |
| 11 | Ben Mowry# | 26 | 2031-2032 | |
| 11 | Jose Pisciotta# | 26 | 2032-2033 | |
| 15 | Catalin Butoiu | 25 | 2024-2029 | |
| 15 | Ramon Carrasco | 25 | 2024-2027 | |
| 15 | Ryan Weiss | 25 | 2019-2021 | |
| 18 | Kristian Cardozo | 24 | 2026-2028 | |
| 18 | Steve France | 24 | 2022-2027 | |
| 18 | Harrison Francis | 24 | 2020-2024 | |
| 18 | Jose Gonzalez# | 24 | 2034-2036 | |
| 18 | Connor Grey | 24 | 2017-2022 | |
| 18 | Jorge Mendez# | 24 | 2032-2036 | |
| 18 | Cody Reed | 24 | 2016-2021 | |
| 25 | Austin Drury | 23 | 2019-2024 | |
| 25 | Mike Hannan | 23 | 2023-2025 | |
| 25 | Jorge Maldonado | 23 | 2028-2029 | |
| 28 | Ryan Atkinson | 22 | 2017-2022 | |
| 28 | Robert Colina | 22 | 2021-2023 | |
| 28 | Manuel Flores | 22 | 2009-2012 | |
| 28 | Chris Noonan# | 22 | 2030-2031 | |
| 28 | Bobby Vonderheide# | 22 | 2029-2031 | |
| 28 | Ben Weekley | 22 | 2030-2033 | |
| 34 | Jake Bork# | 21 | 2032-2035 | |
| 34 | Josh Bowman | 21 | 2012-2014 | |
| 34 | Mike Cabrera | 21 | 2022-2026 | |
| 34 | Francisco Crispin | 21 | 2024-2027 | |
| 34 | Jason Forjet | 21 | 2013-2016 | |
| 34 | Andy Hudspeth# | 21 | 2031-2033 | |
| 34 | Omar Jasso | 21 | 2024-2027 | |
| 34 | Jimmy Lapp | 21 | 2032-2034 | |
| 34 | Brooks McNiven | 21 | 2004-2006 | |
| 34 | Mike Miller# | 21 | 2030-2033 | |
| 34 | Jon Reece | 21 | 2028-2031 | |
| 34 | Danny Rivera | 21 | 2022-2026 | |
| 34 | Luis Saenz# | 21 | 2029-2031 | |
| 34 | Brandon Sinnery | 21 | 2013-2015 | |
| 48 | Chris Bell# | 20 | 2034-2035 | |
| 48 | Denny Brady | 20 | 2019-2021 | |
| 48 | Manny Evangelista# | 20 | 2034-2036 | |
| 48 | Carlos Hernandez | 20 | 2021-2022 | |
| 48 | J.D. Maples# | 20 | 2031-2032 | |
| 48 | Kelvin Marte | 20 | 2010-2013 | |
| 48 | Leon Sainz | 20 | 2022-2025 | |
| 48 | Jesus Silva | 20 | 2002-2006 | |
| 48 | Jim Zitney# | 20 | 2034-2035 | |
| 57 | Tim Alderson | 19 | 2008-2014 | |
| 57 | Chris Comer# | 19 | 2033-2034 | |
| 57 | Alex Custodio | 19 | 2022-2026 | |
| 57 | Mordecai Disraeli# | 19 | 2032-2036 | |
| 57 | Jon Jensen# | 19 | 2027-2028 | |
| 57 | Al Morales | 19 | 2022-2024 | |
| 57 | Joe Rivera | 19 | 2027-2029 | |
| 57 | Bobby Roessler | 19 | 2028-2031 | |
| 57 | Jesus Sanchez# | 19 | 2032-2034 | |
| 57 | Brian Stokes | 19 | 2001-2010 | |
| 57 | Noel Vela | 19 | 2020-2023 | |
| 57 | Pete Walter | 19 | 2028-2032 | |
| 57 | Craig Westcott | 19 | 2010-2011 | |
| 70 | Andrew Barbosa | 18 | 2013-2014 | |
| 70 | Ben Cassata | 18 | 2026-2028 | |
| 70 | Anthony Hoopii-Tuionetoa | 18 | 2025-2028 | |
| 70 | Jim Kimmer# | 18 | 2033-2036 | |
| 70 | Ed Leal# | 18 | 2033-2035 | |
| 70 | Bob Lopez# | 18 | 2035-2036 | |
| 70 | Reggie McClain | 18 | 2017-2019 | |
| 70 | Steve Meyers | 18 | 2023-2026 | |
| 70 | Chris Rago | 18 | 2021-2024 | |
| 70 | Bill Ramirez | 18 | 2029-2032 | |
| 70 | Rod Richard# | 18 | 2031-2036 | |
| 70 | Sam Schmersal | 18 | 2028-2029 | |
| 70 | Mike Zanette# | 18 | 2030-2030 | |
| 83 | Bud Anderson | 17 | 1978-1979 | |
| 83 | Alan Berghaus# | 17 | 2032-2035 | |
| 83 | Jesus Bolivar | 17 | 2026-2027 | |
| 83 | Jose Corniell | 17 | 2025-2026 | |
| 83 | Justin Donatella | 17 | 2016-2021 | |
| 83 | Jamie Feltner | 17 | 2025-2028 | |
| 83 | Dannie Gallagher | 17 | 2029-2032 | |
| 83 | Joe Gatto | 17 | 2017-2020 | |
| 83 | Kennil Gomez | 17 | 2009-2012 | |
| 83 | Brandon Hynick | 17 | 2007-2012 | |
| 83 | Brandon Komar | 17 | 2021-2023 | |
| 83 | Orlando La Caille | 17 | 2034-2034 | |
| 83 | Josh Lizarraga# | 17 | 2032-2034 | |
| 83 | Addison Moss | 17 | 2022-2025 | |
| 83 | Luis Pena | 17 | 2017-2020 | |
| 83 | Ryan Rolison | 17 | 2019-2025 | |
| 83 | Edarian Wise# | 17 | 2034-2036 | |
| 100 | Ben Alsup | 16 | 2013-2014 |
