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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | José Guerra | 1.000 | 2022-2025 | |
| 1 | Natsuo Kono# | 1.000 | 2053-2057 | |
| 1 | José Pezina | 1.000 | 2022-2029 | |
| 1 | Brent Strom# | 1.000 | 2050-2056 | |
| 5 | Jimmy Greenwood | .800 | 2026-2045 | |
| 5 | Félix Hernández | .800 | 2027-2028 | |
| 5 | Javier Velázquez | .800 | 2025-2031 | |
| 8 | Abel Gibson | .750 | 2028-2035 | |
| 8 | Hani Goddard# | .750 | 2044-2054 | |
| 10 | Jorge Cintrón | .667 | 2026-2027 | |
| 10 | José Rosas | .667 | 2027-2031 | |
| 12 | Curtis Barnes | .625 | 2027-2031 | |
| 13 | Juan Acevedo | .600 | 2020-2026 | |
| 13 | Jesús Pacheco | .600 | 2023-2027 | |
| 15 | Harold Aspell | .500 | 2025-2027 | |
| 15 | Salvador Gonzáles | .500 | 2027-2035 | |
| 15 | José López | .500 | 2036-2046 | |
| 15 | Ramiro Medina | .500 | 2050-2054 | |
| 19 | Dan O'Manning | .400 | 2027-2036 | |
| 20 | José Castillo | .250 | 2021-2034 | |
| 21 | Juan Rodríguez | .200 | 2024-2034 | |
| 22 | John Campbell Jr. | .000 | 2028-2036 | |
| 22 | José Gallegos | .000 | 2023-2027 |
