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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Erik Johnson | 63 | 2015-2021 | |
| 2 | Jason Hursh | 54 | 2015-2023 | |
| 3 | Gashie Chiwocha | 53 | 2020-2028 | |
| 4 | Chuck Smith# | 52 | 2022-2035 | |
| 5 | Nick Palewicz | 51 | 2018-2024 | |
| 6 | Kevin Miller | 45 | 2028-2033 | |
| 7 | Jake Cose | 44 | 2016-2020 | |
| 8 | Corey Black | 42 | 2015-2017 | |
| 8 | Nathan Kirby | 42 | 2016-2024 | |
| 10 | Ned Brown | 40 | 2024-2027 | |
| 10 | Derek Massey# | 40 | 2028-2035 | |
| 10 | Daniel Skorpen# | 40 | 2030-2035 | |
| 13 | Junior A. Arias | 38 | 2018-2020 | |
| 14 | Rob Garrett | 36 | 2029-2033 | |
| 14 | Gregory Reinoso | 36 | 2018-2029 | |
| 14 | Santos Rodriguez | 36 | 2015-2021 | |
| 17 | Eric Potts# | 35 | 2030-2035 | |
| 18 | Curt O'Rourke# | 33 | 2032-2035 | |
| 19 | Jake Lemoine | 32 | 2016-2019 | |
| 19 | José Núñez | 32 | 2024-2027 | |
| 19 | Geoff Walters# | 32 | 2024-2032 | |
| 22 | Matt Anderson | 31 | 2015-2026 | |
| 22 | Zach Burdi | 31 | 2017-2025 | |
| 22 | Jesús Guillén | 31 | 2030-2033 | |
| 25 | Paul Blackburn | 30 | 2015-2025 | |
| 25 | Ian McKinney | 30 | 2018-2024 | |
| 25 | Ariel Pena | 30 | 2016-2024 | |
| 28 | Gerard Heerland | 29 | 2028-2031 | |
| 28 | Tyler Loptien | 29 | 2021-2031 | |
| 28 | Kevin Matthews | 29 | 2019-2024 | |
| 31 | Arturo Francisco# | 28 | 2024-2035 | |
| 31 | Stefan Makepeace | 28 | 2025-2029 | |
| 31 | Rubén Morales# | 28 | 2024-2027 | |
| 34 | José Pacheco | 27 | 2023-2033 | |
| 34 | Wes Parsons | 27 | 2016-2018 | |
| 34 | Jake Smith | 27 | 2021-2023 | |
| 37 | Oliver Asencio | 26 | 2022-2024 | |
| 37 | Gus Donovan# | 26 | 2030-2034 | |
| 37 | Trevin Haseltine | 26 | 2017-2024 | |
| 37 | Jeremiah Muhammad | 26 | 2019-2026 | |
| 37 | José Ríos# | 26 | 2029-2035 | |
| 37 | Thyago Vieira | 26 | 2015-2019 | |
| 37 | Willie Walker | 26 | 2024-2027 | |
| 44 | Rob Boyd# | 25 | 2024-2035 | |
| 44 | Jean-Claude Diot | 25 | 2029-2031 | |
| 44 | Dylan Floro | 25 | 2015-2017 | |
| 44 | Johnny Hanson# | 25 | 2033-2035 | |
| 44 | Irving Harden | 25 | 2022-2032 | |
| 44 | Jorge Madrid | 25 | 2026-2031 | |
| 44 | César Mercado | 25 | 2024-2026 | |
| 44 | Chase Mullins | 25 | 2018-2020 | |
| 44 | Rubén Padilla# | 25 | 2030-2035 | |
| 44 | Pierangelo Puggioni | 25 | 2025-2026 | |
| 44 | José Román# | 25 | 2031-2035 | |
| 44 | Aaron Sanchez | 25 | 2015-2019 | |
| 56 | Jimmy Ballard# | 24 | 2028-2035 | |
| 56 | Charlie Dickson# | 24 | 2034-2035 | |
| 56 | Jorge García | 24 | 2021-2025 | |
| 56 | Steve Gare | 24 | 2023-2026 | |
| 56 | Alejandro Lavandero | 24 | 2017-2021 | |
| 56 | Ernie Moore | 24 | 2025-2028 | |
| 56 | Doug Odom | 24 | 2028-2031 | |
| 56 | Aaron Slegers | 24 | 2018-2021 | |
| 56 | Juan Suárez | 24 | 2022-2027 | |
| 65 | Joe Cuda | 23 | 2019-2021 | |
| 65 | Héctor Garza# | 23 | 2030-2035 | |
| 65 | Joey Hankins# | 23 | 2031-2033 | |
| 65 | Jadison Jimenez | 23 | 2019-2021 | |
| 65 | Rob Lewis# | 23 | 2031-2035 | |
| 65 | Enrico Madrid# | 23 | 2032-2035 | |
| 65 | Sammy Wiley# | 23 | 2027-2028 | |
| 72 | Matt Andriese | 22 | 2015-2021 | |
| 72 | Kyle Cody | 22 | 2018-2020 | |
| 72 | Luis González# | 22 | 2028-2030 | |
| 72 | Kurt Heyer | 22 | 2019-2022 | |
| 72 | Raúl Jiménez# | 22 | 2023-2035 | |
| 72 | Luis Manuel Rivera# | 22 | 2030-2033 | |
| 72 | Orlando Romero | 22 | 2027-2030 | |
| 72 | Hunter Wood | 22 | 2017-2020 | |
| 80 | Eric Bright | 21 | 2025-2028 | |
| 80 | José Cruz | 21 | 2030-2032 | |
| 80 | Wilson Delgado | 21 | 2028-2031 | |
| 80 | Tyler Pike | 21 | 2015-2017 | |
| 80 | António Salgado# | 21 | 2033-2035 | |
| 80 | Danny Thomas | 21 | 2020-2024 | |
| 86 | Jeff Ames | 20 | 2015-2020 | |
| 86 | Ron Bailey# | 20 | 2032-2033 | |
| 86 | Garry Collier | 20 | 2026-2027 | |
| 86 | Conner Greene | 20 | 2020-2022 | |
| 86 | Greg Langley# | 20 | 2030-2033 | |
| 86 | Juan Martínez | 20 | 2025-2030 | |
| 86 | Augusto Rodríguez | 20 | 2023-2025 | |
| 86 | Veniamin Ryan# | 20 | 2032-2033 | |
| 86 | Alex Sanabia | 20 | 2015-2017 | |
| 86 | Jimmie Sherfy | 20 | 2016-2027 | |
| 86 | Dusty Smith# | 20 | 2033-2034 | |
| 86 | Gene Smith | 20 | 2023-2034 | |
| 86 | Ernesto Uribe | 20 | 2029-2030 | |
| 86 | Juan Varbuena | 20 | 2026-2029 | |
| 86 | Rob White# | 20 | 2031-2033 |
