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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Gregory Billo | 39 | 2015-2020 | |
| 2 | Augusto Rodríguez# | 37 | 2021-2028 | |
| 2 | Lucas Sims | 37 | 2015-2017 | |
| 4 | Justin Haley | 35 | 2015-2017 | |
| 5 | Jamie Callahan | 33 | 2015-2023 | |
| 6 | Alejandro Viloria | 32 | 2016-2025 | |
| 7 | Sergio Gomez | 31 | 2017-2023 | |
| 7 | Jen-Ho Tseng | 31 | 2016-2017 | |
| 9 | Jake Cose | 30 | 2020-2024 | |
| 9 | Keith Weisenberg | 30 | 2017-2020 | |
| 11 | Yeisson Fernandez | 29 | 2018-2022 | |
| 11 | Jorge Marrero | 29 | 2023-2027 | |
| 11 | Ryan Rodebaugh | 29 | 2018-2024 | |
| 14 | Andrew Bellatti | 28 | 2017-2022 | |
| 14 | Ben Douglas | 28 | 2023-2024 | |
| 14 | José López | 28 | 2021-2027 | |
| 14 | Thaddius Lowry | 28 | 2018-2021 | |
| 14 | Fernando Soler | 28 | 2018-2022 | |
| 19 | Felix Sterling | 27 | 2021-2025 | |
| 20 | Joe Carnes# | 26 | 2027-2029 | |
| 20 | Tyler Loptien# | 26 | 2019-2025 | |
| 20 | Wilbert Minogue | 26 | 2020-2024 | |
| 23 | Oliver Asencio | 25 | 2021-2026 | |
| 23 | Juan Canseco | 25 | 2025-2027 | |
| 23 | António López# | 25 | 2026-2029 | |
| 26 | Robinson Baca# | 24 | 2023-2029 | |
| 26 | Mauricio Cabrera | 24 | 2015-2016 | |
| 26 | John Walter | 24 | 2015-2022 | |
| 29 | Mitch Brown | 23 | 2015-2016 | |
| 29 | Eric Hanhold | 23 | 2017-2020 | |
| 29 | Casey Shane | 23 | 2015-2021 | |
| 29 | Steve Simpson | 23 | 2022-2026 | |
| 29 | Teddy Stankiewicz | 23 | 2016-2019 | |
| 34 | Garrett Fulenchek | 22 | 2018-2022 | |
| 34 | José Magdalena | 22 | 2024-2028 | |
| 34 | Josh Sborz | 22 | 2019-2021 | |
| 34 | Rod Shannon | 22 | 2024-2026 | |
| 38 | Yunior Marte | 21 | 2018-2020 | |
| 38 | Ernesto Sánchez | 21 | 2023-2025 | |
| 38 | Justin Sinibaldi | 21 | 2020-2021 | |
| 38 | Nik Turley | 21 | 2017-2021 | |
| 38 | Rob Woods# | 21 | 2027-2029 | |
| 43 | Alec Grosser | 20 | 2017-2027 | |
| 43 | Albert Martínez# | 20 | 2020-2022 | |
| 43 | Bob Mathews | 20 | 2021-2025 | |
| 43 | Luis Ortíz# | 20 | 2027-2028 | |
| 43 | Mario Paredes# | 20 | 2025-2026 | |
| 43 | José Vázquez# | 20 | 2025-2027 | |
| 43 | Juan Villalobos# | 20 | 2028-2029 | |
| 50 | Anderson Espinoza# | 19 | 2018-2018 | |
| 50 | Divino Gamarra# | 19 | 2024-2029 | |
| 50 | Jose Morel | 19 | 2018-2024 | |
| 50 | Kevin Ramsey# | 19 | 2023-2028 | |
| 50 | Lou Wolfe | 19 | 2023-2027 | |
| 55 | Phil Brooks# | 18 | 2023-2024 | |
| 55 | Porter Clayton | 18 | 2017-2024 | |
| 55 | Juan Cruz# | 18 | 2023-2027 | |
| 55 | Jeff Hays | 18 | 2026-2027 | |
| 55 | Tomas Leoncio | 18 | 2016-2023 | |
| 55 | Dillon Maples | 18 | 2016-2017 | |
| 55 | James Marvel | 18 | 2019-2020 | |
| 55 | Jose Nina | 18 | 2018-2020 | |
| 55 | José Ramírez | 18 | 2023-2025 | |
| 55 | Wilson Requena | 18 | 2022-2024 | |
| 55 | José Rodríguez | 18 | 2022-2028 | |
| 66 | Lou Callahan | 17 | 2024-2026 | |
| 66 | Derek Casey | 17 | 2027-2027 | |
| 66 | Ken Escamilla# | 17 | 2021-2022 | |
| 66 | Pedro Fernandez | 17 | 2016-2019 | |
| 66 | Zach Isler | 17 | 2016-2022 | |
| 66 | Turner Larkins | 17 | 2017-2018 | |
| 66 | Brandon Leibrandt | 17 | 2016-2018 | |
| 66 | Micah Miniard | 17 | 2021-2023 | |
| 66 | Sean O'Neal | 17 | 2022-2027 | |
| 66 | Wes Parsons | 17 | 2015-2015 | |
| 66 | Juan Ramírez# | 17 | 2025-2028 | |
| 66 | Tomás Romero# | 17 | 2024-2026 | |
| 66 | Jake Smith | 17 | 2020-2020 | |
| 66 | Wyatt Strahan | 17 | 2021-2025 | |
| 66 | Raúl Zapata | 17 | 2021-2025 | |
| 81 | Trevor Clifton | 16 | 2018-2019 | |
| 81 | Joel Conner | 16 | 2022-2023 | |
| 81 | Gianlorenzo Figura# | 16 | 2026-2029 | |
| 81 | Curt Fish# | 16 | 2028-2029 | |
| 81 | César Pérez# | 16 | 2021-2022 | |
| 81 | R.J. Reed# | 16 | 2019-2021 | |
| 81 | Tony Reyes | 16 | 2025-2026 | |
| 81 | Alex Richards | 16 | 2020-2022 | |
| 81 | Jorge Rocha# | 16 | 2024-2027 | |
| 81 | Brad Wegman | 16 | 2017-2020 | |
| 91 | Trey Ball | 15 | 2015-2016 | |
| 91 | Chris Beck | 15 | 2015-2018 | |
| 91 | Ernesto Castillo# | 15 | 2026-2029 | |
| 91 | Miguel Angel Chárvez | 15 | 2023-2024 | |
| 91 | Luis Gil | 15 | 2021-2026 | |
| 91 | Foster Griffin | 15 | 2019-2022 | |
| 91 | Dutch Hintz# | 15 | 2028-2029 | |
| 91 | Kyle Kemp | 15 | 2018-2018 | |
| 91 | César Mercado# | 15 | 2025-2026 | |
| 91 | José Ramírez# | 15 | 2024-2029 |
