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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Armando Ortíz | .683 | 2021-2025 | |
| 2 | Carl MacPherson# | .583 | 2031-2035 | |
| 3 | Edward Scarborough | .509 | 2026-2029 | |
| 4 | Kent Horton# | .418 | 2030-2032 | |
| 5 | Phillip Donoghue | .388 | 2029-2033 |
