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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Augusto Salazar# | .933 | 2044-2046 | |
| 2 | Roberto García# | .750 | 2040-2043 | |
| 3 | Emory Sawyer# | .692 | 2042-2045 | |
| 4 | Emílio Deleón | .647 | 2040-2043 | |
| 5 | José Marte# | .643 | 2044-2046 | |
| 6 | Craig Hoover# | .571 | 2037-2040 | |
| 7 | Ismael Díaz | .545 | 2041-2043 | |
| 8 | Adam Burkett# | .538 | 2036-2039 | |
| 9 | Marc Franco | .529 | 2038-2042 | |
| 10 | Tommy MacNeill | .412 | 2035-2037 | |
| 11 | Joe MacAslan# | .350 | 2035-2038 |
