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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Job MacDonald# | 2 | 2097-2098 | |
| 2 | Troy Anderson# | 1 | 2098-2098 | |
| 2 | Josh Carr# | 1 | 2097-2098 | |
| 2 | Victor Castorena# | 1 | 2097-2098 | |
| 2 | Tim Demaree# | 1 | 2098-2098 | |
| 2 | Jason Havens# | 1 | 2097-2098 | |
| 2 | Matt Kotansky# | 1 | 2095-2098 | |
| 2 | Jason Lento# | 1 | 2097-2098 | |
| 2 | Eddie Melendez# | 1 | 2098-2098 | |
| 2 | Josh Montgomery# | 1 | 2098-2098 | |
| 2 | Brad Phillips# | 1 | 2098-2098 | |
| 2 | Willie Portugal# | 1 | 2096-2098 | |
| 2 | Harry Reid# | 1 | 2098-2098 | |
| 2 | Julio Rolon# | 1 | 2098-2098 | |
| 15 | Jesse Aguiar# | 0 | 2098-2098 | |
| 15 | Gene Allen# | 0 | 2098-2098 | |
| 15 | Justin Ammons# | 0 | 2093-2098 | |
| 15 | Ronnie Birdsall# | 0 | 2093-2098 | |
| 15 | Mike Bivona# | 0 | 2095-2098 | |
| 15 | Willie Campos# | 0 | 2095-2098 | |
| 15 | Bill Caudell# | 0 | 2096-2098 | |
| 15 | Francisco Cruz# | 0 | 2098-2098 | |
| 15 | Alex Escalera# | 0 | 2098-2098 | |
| 15 | Scott Galvin# | 0 | 2098-2098 | |
| 15 | Yukio Ito# | 0 | 2095-2098 | |
| 15 | Andy Losinski# | 0 | 2097-2098 | |
| 15 | R.J. Louvier# | 0 | 2097-2098 | |
| 15 | Jason Minton# | 0 | 2098-2098 | |
| 15 | Tony Negron# | 0 | 2098-2098 | |
| 15 | Amari Pedicone# | 0 | 2096-2098 | |
| 15 | Tony Rios# | 0 | 2098-2098 | |
| 15 | Ruben Ruiz# | 0 | 2098-2098 | |
| 15 | Daniel Santa Cruz# | 0 | 2098-2098 | |
| 15 | Joe Yount# | 0 | 2098-2098 |
