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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | David Davis# | 43 | 2019-2029 | |
| 2 | Mike Barrett | 37 | 2022-2027 | |
| 3 | José Cabrera# | 35 | 2025-2028 | |
| 4 | Jesús López | 33 | 2016-2023 | |
| 4 | Bob McGhee# | 33 | 2015-2028 | |
| 6 | R.J. Anderson# | 31 | 2020-2027 | |
| 7 | Shawn Arnold# | 30 | 2015-2022 | |
| 7 | William Bonner# | 30 | 2020-2027 | |
| 7 | Scott Mildren# | 30 | 2024-2027 | |
| 7 | Júlio Palácios | 30 | 2021-2026 | |
| 11 | Woo-suk Cho# | 29 | 2026-2029 | |
| 11 | Josh Gardner | 29 | 2017-2021 | |
| 13 | Clay Clark | 28 | 2015-2018 | |
| 13 | Cisco Ortíz# | 28 | 2025-2029 | |
| 15 | Brent Riley | 27 | 2015-2025 | |
| 16 | Travis Carson# | 26 | 2020-2021 | |
| 16 | Cisco Romero | 26 | 2019-2022 | |
| 16 | Pedro Romero | 26 | 2020-2026 | |
| 16 | Rob Smith# | 26 | 2018-2027 | |
| 20 | Jorge Carrión# | 25 | 2022-2026 | |
| 20 | Jeff Moore | 25 | 2020-2022 | |
| 20 | Javier Roldán# | 25 | 2019-2023 | |
| 20 | Mark Tucker# | 25 | 2017-2021 | |
| 24 | César González# | 24 | 2021-2023 | |
| 24 | Chris Hayes# | 24 | 2023-2027 | |
| 24 | Louis McDowell# | 24 | 2015-2028 | |
| 24 | Eric Patnode | 24 | 2016-2025 | |
| 28 | Jason Ackerman | 23 | 2015-2022 | |
| 28 | Álex Carrillo | 23 | 2018-2021 | |
| 28 | António Fabián# | 23 | 2020-2028 | |
| 28 | Homer O'Lannigan | 23 | 2018-2021 | |
| 28 | Hartmann Riedman# | 23 | 2024-2027 | |
| 28 | Alex Simmons | 23 | 2017-2024 | |
| 34 | Chris Burgess# | 22 | 2022-2027 | |
| 34 | Atila Freska# | 22 | 2026-2028 | |
| 34 | Gerald Keller# | 22 | 2026-2029 | |
| 34 | Miguel López# | 22 | 2026-2028 | |
| 34 | Homer Shafer | 22 | 2015-2020 | |
| 34 | Ray Thibaut | 22 | 2015-2019 | |
| 34 | José Vargo# | 22 | 2022-2024 | |
| 34 | Steven Williams | 22 | 2015-2019 | |
| 42 | Elmer García# | 21 | 2021-2028 | |
| 42 | Ralph Haggerty# | 21 | 2027-2029 | |
| 42 | Peter Hall# | 21 | 2024-2028 | |
| 42 | Mike Russell | 21 | 2018-2022 | |
| 42 | Maxwell Simon# | 21 | 2024-2027 | |
| 47 | Paul Addison# | 20 | 2027-2029 | |
| 47 | Xavier Andrade | 20 | 2017-2022 | |
| 47 | Emory Bryant | 20 | 2015-2019 | |
| 47 | Tom Hernández | 20 | 2016-2021 | |
| 47 | Carlos Peret# | 20 | 2025-2028 | |
| 47 | Bartolo Ramírez# | 20 | 2019-2023 | |
| 47 | Wilson Vélez# | 20 | 2016-2022 | |
| 54 | Ken Carter | 19 | 2015-2016 | |
| 54 | Joe Lynn | 19 | 2018-2023 | |
| 54 | Richard Meyer | 19 | 2017-2021 | |
| 54 | Paul Nance | 19 | 2015-2025 | |
| 54 | José Ortíz# | 19 | 2024-2026 | |
| 59 | Sid Brown# | 18 | 2017-2023 | |
| 59 | Victor de Meij# | 18 | 2025-2029 | |
| 59 | Freddy González | 18 | 2015-2020 | |
| 59 | Anthony Hanover# | 18 | 2016-2020 | |
| 59 | Greg Kelly | 18 | 2016-2020 | |
| 59 | Delmar Llerena# | 18 | 2026-2029 | |
| 59 | Alonso Rodríguez | 18 | 2015-2019 | |
| 59 | Yoriyoshi Yoshimura# | 18 | 2028-2029 | |
| 67 | Steve Bryan# | 17 | 2019-2029 | |
| 67 | Woody Carlson# | 17 | 2018-2020 | |
| 67 | Norberto Concepción# | 17 | 2027-2028 | |
| 67 | Luis Fernández | 17 | 2015-2024 | |
| 67 | King Fletcher# | 17 | 2020-2023 | |
| 67 | Doug Green# | 17 | 2018-2020 | |
| 67 | Jesús Guerra# | 17 | 2026-2028 | |
| 67 | Gabriel Herrera# | 17 | 2026-2028 | |
| 67 | Teddy Jones | 17 | 2017-2019 | |
| 67 | Oswaldo Mobray# | 17 | 2023-2024 | |
| 67 | Travis Nelson# | 17 | 2024-2029 | |
| 67 | José Rodríguez | 17 | 2015-2019 | |
| 67 | John Shirley | 17 | 2018-2025 | |
| 67 | Artie Taylor | 17 | 2017-2018 | |
| 67 | Eric Taylor | 17 | 2019-2021 | |
| 67 | Elroy Thompkins# | 17 | 2026-2027 | |
| 67 | José Trujillo | 17 | 2016-2019 | |
| 67 | Orlando Uribe# | 17 | 2025-2028 | |
| 67 | Gabriel Valenzuela# | 17 | 2026-2029 | |
| 67 | Louis Webber | 17 | 2016-2019 | |
| 67 | Brad Wilson | 17 | 2015-2021 | |
| 88 | José Barajas# | 16 | 2022-2025 | |
| 88 | Nick Blount | 16 | 2016-2019 | |
| 88 | John Boyle | 16 | 2017-2022 | |
| 88 | Robert Byrd | 16 | 2017-2023 | |
| 88 | Iván Castillo | 16 | 2015-2018 | |
| 88 | Enrique Castro# | 16 | 2028-2028 | |
| 88 | Hubert Dunham# | 16 | 2016-2027 | |
| 88 | Gonzalo Granados | 16 | 2020-2025 | |
| 88 | Joe Griffin# | 16 | 2024-2026 | |
| 88 | Ryan McCall# | 16 | 2022-2025 | |
| 88 | Lester Sullivan# | 16 | 2021-2021 | |
| 88 | Salvador Torres# | 16 | 2026-2029 | |
| 100 | John Adams | 15 | 2016-2022 |
