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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Tony Gilbert# | 1 | 2026-2026 | |
| 1 | Bob Gustin# | 1 | 2026-2026 | |
| 1 | Bret Rini# | 1 | 2025-2026 | |
| 1 | Mike Wheatley# | 1 | 2026-2026 | |
| 5 | Mat Bryde# | 0 | 2026-2026 | |
| 5 | Robby Coulter# | 0 | 2025-2026 | |
| 5 | Josh Davis# | 0 | 2025-2026 | |
| 5 | Willie Felix# | 0 | 2026-2026 | |
| 5 | Brandon Hudson# | 0 | 2026-2026 | |
| 5 | Billy Koltiska# | 0 | 2026-2026 | |
| 5 | Nestor Malyutkin# | 0 | 2026-2026 | |
| 5 | Andy Martin# | 0 | 2026-2026 | |
| 5 | Adam McCarthy# | 0 | 2026-2026 | |
| 5 | Josh Meyer# | 0 | 2026-2026 | |
| 5 | Jesus Preciado# | 0 | 2026-2026 | |
| 5 | Corey Schrum# | 0 | 2026-2026 | |
| 5 | Nate Stinchcomb# | 0 | 2026-2026 | |
| 5 | Rory Sweet# | 0 | 2025-2026 | |
| 5 | Pat Tanner# | 0 | 2025-2026 | |
| 5 | Adam Teare# | 0 | 2025-2026 | |
| 5 | Jerome Watts# | 0 | 2026-2026 |
