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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Career Leaderboard |
|---|---|---|---|---|
| 1 | Tim Black | 18 | 2028 | |
| 2 | Jim O'Brien | 17 | 2019 | |
| 2 | Jim Smith | 17 | 2021 | |
| 4 | Dian Alisjahbana | 15 | 2019 | |
| 4 | Jim Smith | 15 | 2022 | |
| 4 | Alex Bond | 15 | 2025 | |
| 7 | Steve Helms | 14 | 2023 | |
| 7 | Pete Wilson* | 14 | 2019 | |
| 7 | Ed Fisher | 14 | 2022 | |
| 7 | Gaston Lépine | 14 | 2021 | |
| 7 | Reginald Newell | 14 | 2018 | |
| 7 | Sergio Guardado | 14 | 2021 | |
| 7 | Ken Smith | 14 | 2027 | |
| 7 | Alan Teeters | 14 | 2019 | |
| 7 | Jeremy Emery* | 14 | 2020 | |
| 16 | Curt Kennedy | 13 | 2017 | |
| 16 | Rubén Soto | 13 | 2020 | |
| 16 | Rubén Soto | 13 | 2019 | |
| 16 | Steve Bowles | 13 | 2021 | |
| 16 | José Garza | 13 | 2018 | |
| 16 | Aurelio García | 13 | 2023 | |
| 16 | António Rodríguez | 13 | 2018 | |
| 23 | Tim Farley | 12 | 2021 | |
| 23 | Tony Ramírez | 12 | 2029 | |
| 23 | Jim Coleman | 12 | 2023 | |
| 23 | Harland Guillou | 12 | 2045 | |
| 23 | Ron Nelson | 12 | 2020 | |
| 23 | Ken Miller | 12 | 2017 | |
| 23 | Luis Pérez | 12 | 2022 | |
| 23 | Teinosuke Yoshida | 12 | 2018 | |
| 23 | Joey Daniels | 12 | 2017 | |
| 23 | Bobby Dodson | 12 | 2020 | |
| 23 | Sancho Gonzáles | 12 | 2022 | |
| 23 | Norm Brown | 12 | 2029 | |
| 23 | Carl Carr | 12 | 2032 | |
| 23 | Don MacGruder | 12 | 2019 | |
| 23 | Mike Turner | 12 | 2023 | |
| 23 | José Sánchez | 12 | 2027 | |
| 23 | Ed Jenkins | 12 | 2022 | |
| 23 | Juan Morales | 12 | 2029 | |
| 23 | Ken Miller | 12 | 2018 | |
| 23 | Kevin Parker | 12 | 2023 | |
| 23 | Ben Jones | 12 | 2020 | |
| 44 | Mike Welsh | 11 | 2022 | |
| 44 | Joe Crowder | 11 | 2017 | |
| 44 | Bo McDonald | 11 | 2018 | |
| 44 | Juan Villa | 11 | 2023 | |
| 44 | Luis Pérez | 11 | 2021 | |
| 44 | Pete Wilson* | 11 | 2018 | |
| 44 | Eric Horton | 11 | 2019 | |
| 44 | Rocky Robbins | 11 | 2022 | |
| 44 | Don MacGruder | 11 | 2020 | |
| 44 | Bob Osborne | 11 | 2019 | |
| 44 | Teinosuke Yoshida | 11 | 2020 | |
| 44 | Andy Ryan | 11 | 2017 | |
| 44 | Tim Black | 11 | 2027 | |
| 44 | Jeremy Emery* | 11 | 2019 | |
| 44 | Phil Anderson | 11 | 2041 | |
| 44 | Steeve Hardy | 11 | 2021 | |
| 44 | Charlie Hart | 11 | 2018 | |
| 44 | Vic Dacres | 11 | 2044 | |
| 44 | Ken Smith | 11 | 2026 | |
| 44 | Robbie Roberts | 11 | 2017 | |
| 44 | Wilson Pérez | 11 | 2028 | |
| 44 | Ron Wilkerson | 11 | 2025 | |
| 44 | Tim Wilder | 11 | 2022 | |
| 44 | Tim Wilder | 11 | 2021 | |
| 44 | Joey Daniels | 11 | 2020 | |
| 44 | Dave Wolf | 11 | 2023 | |
| 44 | Tony Erwin | 11 | 2018 | |
| 44 | Geoff Melsom | 11 | 2017 | |
| 44 | Chris Duke | 11 | 2046 | |
| 44 | Jamie Martin | 11 | 2017 | |
| 44 | Jamie Morris | 11 | 2017 | |
| 44 | Greg Davis | 11 | 2017 | |
| 44 | Freddy López | 11 | 2018 | |
| 77 | Brad Anderson | 10 | 2020 | |
| 77 | Tim Gibson# | 10 | 2047 | |
| 77 | Teinosuke Yoshida | 10 | 2019 | |
| 77 | Stu Hamilton | 10 | 2020 | |
| 77 | Jimmy Horn | 10 | 2019 | |
| 77 | Bob Allen | 10 | 2020 | |
| 77 | Ron Wilkerson | 10 | 2023 | |
| 77 | Isaac Roberts | 10 | 2023 | |
| 77 | Jim Joseph | 10 | 2044 | |
| 77 | Luis Díaz | 10 | 2021 | |
| 77 | Steve Medina | 10 | 2021 | |
| 77 | Eric Spencer | 10 | 2028 | |
| 77 | Jeff Mitchell | 10 | 2043 | |
| 77 | José Garza | 10 | 2017 | |
| 77 | Gil Adams | 10 | 2025 | |
| 77 | Eric Horton | 10 | 2018 | |
| 77 | Garry Coleman | 10 | 2018 | |
| 77 | Bob Martin | 10 | 2020 | |
| 77 | Donnie Skinner | 10 | 2020 | |
| 77 | Kevin Parker | 10 | 2022 | |
| 77 | Jim Coleman | 10 | 2022 | |
| 77 | Jared Corbin | 10 | 2023 | |
| 77 | Juan Arroyo | 10 | 2020 | |
| 77 | Juan García | 10 | 2020 |
