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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Career Leaderboard |
|---|---|---|---|---|
| 1 | Derrick Jones# | 2 | 2046 | |
| 2 | Micheal Bly# | 1 | 2046 | |
| 2 | Foeke Reus# | 1 | 2046 | |
| 2 | Greg Ayala# | 1 | 2046 | |
| 5 | Víctor Trujillo# | 0 | 2046 | |
| 5 | Jon Smith# | 0 | 2046 | |
| 5 | Artie Hankins# | 0 | 2046 | |
| 5 | Carlos Piñeiro# | 0 | 2046 | |
| 5 | Virgil Gilbert# | 0 | 2046 | |
| 5 | Tom Palanirajan# | 0 | 2046 | |
| 5 | Tyrone Tolbert# | 0 | 2046 | |
| 5 | Carl McCoy# | 0 | 2046 | |
| 5 | Ronald Love# | 0 | 2046 | |
| 5 | Pat Harmon# | 0 | 2046 | |
| 5 | Todd James# | 0 | 2046 | |
| 5 | Ron Holland# | 0 | 2046 | |
| 5 | Steve Gourin# | 0 | 2046 | |
| 5 | Francisco Díaz# | 0 | 2046 |
