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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jerry Matthews# | 13 | 2035-2040 | |
| 2 | Brian Christian# | 9 | 2035-2041 | |
| 3 | T.J. Johnson# | 8 | 2040-2041 | |
| 4 | Josh Conway# | 7 | 2038-2040 | |
| 4 | Ben Peter | 7 | 2035-2036 | |
| 6 | Ben Exley# | 6 | 2039-2041 | |
| 6 | Mark Vecchio# | 6 | 2036-2039 | |
| 8 | Jose Garcia | 5 | 2035-2037 | |
| 8 | Jim Herrick# | 5 | 2038-2038 | |
| 8 | Corey Palmer | 5 | 2034-2035 | |
| 8 | Ricardo Rossito | 5 | 2038-2038 | |
| 12 | Alberto Aranda | 4 | 2033-2033 | |
| 12 | Ricky Arriola# | 4 | 2039-2040 | |
| 12 | Adam Brown | 4 | 2037-2037 | |
| 12 | Kurat Feyzioglu# | 4 | 2034-2039 | |
| 12 | Brett Gross | 4 | 2034-2034 | |
| 12 | Ricky Hernandez# | 4 | 2041-2041 | |
| 12 | Miguel Leon | 4 | 2034-2034 | |
| 12 | Nelson Ramos | 4 | 2033-2033 | |
| 12 | Kevin Renninger# | 4 | 2038-2038 | |
| 12 | Juan Rodriguez# | 4 | 2040-2041 | |
| 12 | Curtis Weidman | 4 | 2035-2035 | |
| 23 | Ira Aguilar# | 3 | 2034-2034 | |
| 23 | Wayne Ayler | 3 | 2033-2033 | |
| 23 | Chad Britt | 3 | 2032-2032 | |
| 23 | Tommy Esparza | 3 | 2033-2033 | |
| 23 | Omar Garcia# | 3 | 2036-2037 | |
| 23 | Mauricio Herrera | 3 | 2035-2035 | |
| 23 | Mario Marin# | 3 | 2041-2041 | |
| 23 | Josh McMahon | 3 | 2033-2037 | |
| 23 | Joey Roberts# | 3 | 2037-2037 | |
| 23 | Francisco Rodriguez | 3 | 2036-2036 | |
| 23 | Edgar Torres | 3 | 2034-2034 | |
| 34 | Wilson Ballinas# | 2 | 2039-2040 | |
| 34 | Flinn Berthelsen# | 2 | 2039-2041 | |
| 34 | Matt Causey | 2 | 2033-2033 | |
| 34 | Enrique Giraldo# | 2 | 2039-2041 | |
| 34 | Alex Huertas | 2 | 2038-2040 | |
| 34 | Randy Letson# | 2 | 2036-2036 | |
| 34 | Jarred Mann | 2 | 2035-2035 | |
| 34 | Mike Matter | 2 | 2033-2033 | |
| 34 | Adam O'Rourke | 2 | 2034-2034 | |
| 34 | Joe Rice# | 2 | 2041-2041 | |
| 34 | Enrique Sandoval | 2 | 2035-2036 | |
| 34 | Gary Veilleux# | 2 | 2036-2036 | |
| 46 | Joe Braun# | 1 | 2036-2036 | |
| 46 | Omar Chavez# | 1 | 2034-2035 | |
| 46 | Bill Guyett# | 1 | 2041-2041 | |
| 46 | Chi-hyeon Jang# | 1 | 2041-2041 | |
| 46 | Rafael Marin | 1 | 2034-2034 | |
| 46 | Bill Muscott | 1 | 2037-2037 | |
| 46 | Rich Richmond# | 1 | 2038-2038 | |
| 46 | Kyle Rogers# | 1 | 2039-2041 | |
| 46 | Chance Welch | 1 | 2039-2039 | |
| 55 | Dirk Buffy | 0 | 2036-2036 | |
| 55 | Ralph Burdick | 0 | 2035-2035 | |
| 55 | Jake Butler# | 0 | 2041-2041 | |
| 55 | Arturo Espejo# | 0 | 2040-2040 | |
| 55 | Roberto Garcia | 0 | 2038-2038 | |
| 55 | Mike Hood | 0 | 2033-2033 | |
| 55 | Nelson Manriquez# | 0 | 2035-2035 | |
| 55 | C.J. Morgan# | 0 | 2038-2038 | |
| 55 | Chris Phillips# | 0 | 2040-2040 | |
| 55 | Josh Selby | 0 | 2035-2035 | |
| 55 | Larry Tiffany | 0 | 2036-2036 | |
| 55 | Houston Weinreb# | 0 | 2037-2039 | |
| 55 | Alik Zekkel# | 0 | 2039-2039 |
