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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Career Leaderboard |
|---|---|---|---|---|
| 1 | Ivan Puentes# | 3 | 2098 | |
| 2 | Malik Olds# | 1 | 2098 | |
| 2 | Karl Morgan# | 1 | 2098 | |
| 2 | Kevin Ewing# | 1 | 2098 | |
| 2 | Matt Martin# | 1 | 2098 | |
| 2 | A.J. Wayne# | 1 | 2098 | |
| 2 | Tony Olivarez# | 1 | 2098 | |
| 2 | Lindsay Nickerson# | 1 | 2098 | |
| 2 | Bobby Lopez# | 1 | 2098 | |
| 2 | Javier Amaya# | 1 | 2098 | |
| 2 | Travis Crum# | 1 | 2098 | |
| 2 | Billy Kamp# | 1 | 2098 | |
| 2 | Beau Rohmer# | 1 | 2098 | |
| 14 | Tyler Allen# | 0 | 2098 | |
| 14 | Jake Conti# | 0 | 2098 | |
| 14 | Jose Hernandes# | 0 | 2098 | |
| 14 | Yorfran Carnes# | 0 | 2098 | |
| 14 | Alex Reyes# | 0 | 2098 | |
| 14 | Brian Denning# | 0 | 2098 | |
| 14 | Miguel Corral# | 0 | 2098 | |
| 14 | Antonio Zaragoza# | 0 | 2098 | |
| 14 | Kevin Main# | 0 | 2098 | |
| 14 | Gerardo Alvarado# | 0 | 2098 | |
| 14 | Demetrio Borcellino# | 0 | 2098 | |
| 14 | Kevin Peterson# | 0 | 2098 | |
| 14 | Josh Carey# | 0 | 2098 | |
| 14 | Will Hinton# | 0 | 2098 | |
| 14 | Jason Pressley# | 0 | 2098 | |
| 14 | Ben Mills# | 0 | 2098 | |
| 14 | Jason Webb# | 0 | 2098 | |
| 14 | Daniel Ortiz# | 0 | 2098 | |
| 14 | Jerry Bandelow# | 0 | 2098 | |
| 14 | Clay Self# | 0 | 2098 | |
| 14 | Matt Trosclair# | 0 | 2098 | |
| 14 | Alex Medrano# | 0 | 2098 | |
| 14 | Carlos Valencia# | 0 | 2098 | |
| 14 | Mike Sweigart# | 0 | 2098 | |
| 14 | Mario Lausell# | 0 | 2098 |
