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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Ben Kitch# | 18 | 2047-2050 | |
| 2 | Jerry Matthews | 13 | 2035-2040 | |
| 3 | Brian Christian | 12 | 2035-2043 | |
| 3 | T.J. Johnson | 12 | 2040-2042 | |
| 5 | Matt Rockmore# | 11 | 2048-2050 | |
| 6 | Justin Gray# | 10 | 2046-2048 | |
| 6 | Juan Rodriguez | 10 | 2040-2043 | |
| 8 | Matt Poole# | 9 | 2049-2050 | |
| 8 | Mark Vecchio | 9 | 2036-2043 | |
| 10 | Ricky Arriola | 8 | 2039-2042 | |
| 10 | Mario Marin | 8 | 2041-2043 | |
| 12 | Calvin Birley | 7 | 2045-2045 | |
| 12 | Josh Conway | 7 | 2038-2040 | |
| 12 | Ben Peter | 7 | 2035-2036 | |
| 12 | Yakir Roman# | 7 | 2049-2050 | |
| 16 | Fernando Alvarez | 6 | 2044-2044 | |
| 16 | Alberto Camacho | 6 | 2043-2044 | |
| 16 | Jorge de la Torre# | 6 | 2046-2046 | |
| 16 | Ben Exley | 6 | 2039-2041 | |
| 16 | Steve Feix# | 6 | 2051-2051 | |
| 16 | Tony Fernandez | 6 | 2046-2046 | |
| 16 | Tom Markee | 6 | 2045-2045 | |
| 16 | Miguel Mayen# | 6 | 2050-2050 | |
| 16 | Tyler Robinson# | 6 | 2051-2051 | |
| 16 | Brad Sleezer# | 6 | 2050-2050 | |
| 16 | Nick Taylor# | 6 | 2051-2051 | |
| 27 | Edwin Esquivel | 5 | 2047-2047 | |
| 27 | Jose Garcia | 5 | 2035-2037 | |
| 27 | Bill Guyett | 5 | 2041-2043 | |
| 27 | Jim Herrick | 5 | 2038-2038 | |
| 27 | Eric O'Hara | 5 | 2048-2048 | |
| 27 | Corey Palmer | 5 | 2034-2035 | |
| 27 | Tony Perez# | 5 | 2051-2051 | |
| 27 | Jeff Rabinowitz# | 5 | 2045-2045 | |
| 27 | Bryan Rice# | 5 | 2051-2051 | |
| 27 | Miguel Rios# | 5 | 2048-2048 | |
| 27 | Santiago Robles | 5 | 2045-2045 | |
| 27 | Ricardo Rossito | 5 | 2038-2038 | |
| 27 | Chris Shewey# | 5 | 2049-2049 | |
| 27 | Jason Thomas | 5 | 2045-2045 | |
| 27 | Ruben Torres | 5 | 2044-2044 | |
| 27 | Braxton Wallace | 5 | 2044-2044 | |
| 43 | Alberto Aranda | 4 | 2033-2033 | |
| 43 | Adam Brown | 4 | 2037-2037 | |
| 43 | Alex Camarillo | 4 | 2048-2048 | |
| 43 | Kurat Feyzioglu# | 4 | 2034-2042 | |
| 43 | Brett Gross | 4 | 2034-2034 | |
| 43 | Ricky Hernandez | 4 | 2041-2041 | |
| 43 | Miguel Leon | 4 | 2034-2034 | |
| 43 | Doug Maag | 4 | 2046-2046 | |
| 43 | Jon Orozco | 4 | 2046-2046 | |
| 43 | Nelson Ramos | 4 | 2033-2033 | |
| 43 | Kevin Renninger | 4 | 2038-2038 | |
| 43 | Curtis Weidman | 4 | 2035-2035 | |
| 55 | Chris Adams | 3 | 2048-2048 | |
| 55 | Ira Aguilar | 3 | 2034-2034 | |
| 55 | Wayne Ayler | 3 | 2033-2033 | |
| 55 | Chad Britt | 3 | 2032-2032 | |
| 55 | Quadir Brown# | 3 | 2048-2050 | |
| 55 | Tommy Esparza | 3 | 2033-2033 | |
| 55 | Omar Garcia | 3 | 2036-2037 | |
| 55 | Zeke Hernandez | 3 | 2040-2044 | |
| 55 | Mauricio Herrera | 3 | 2035-2035 | |
| 55 | Randy Letson | 3 | 2036-2043 | |
| 55 | Ken Mason | 3 | 2049-2050 | |
| 55 | Josh McMahon | 3 | 2033-2037 | |
| 55 | Bryant Patterson | 3 | 2042-2042 | |
| 55 | Joey Roberts | 3 | 2037-2037 | |
| 55 | Francisco Rodriguez | 3 | 2036-2036 | |
| 55 | Edgar Torres | 3 | 2034-2034 | |
| 71 | Adam Auger# | 2 | 2049-2049 | |
| 71 | Wilson Ballinas | 2 | 2039-2040 | |
| 71 | Flinn Berthelsen | 2 | 2039-2043 | |
| 71 | Matt Causey | 2 | 2033-2033 | |
| 71 | Enrique Giraldo | 2 | 2039-2041 | |
| 71 | Chandler Grice | 2 | 2047-2048 | |
| 71 | Alex Harper# | 2 | 2048-2049 | |
| 71 | Alex Huertas | 2 | 2038-2040 | |
| 71 | Logan Itterly | 2 | 2042-2042 | |
| 71 | Pedro Lopez# | 2 | 2049-2049 | |
| 71 | Rogelio Lopez | 2 | 2047-2047 | |
| 71 | Arturo Mancera | 2 | 2042-2043 | |
| 71 | Jarred Mann | 2 | 2035-2035 | |
| 71 | Mike Matter | 2 | 2033-2033 | |
| 71 | Gaetan Noe | 2 | 2043-2043 | |
| 71 | Adam O'Rourke | 2 | 2034-2034 | |
| 71 | Joe Rice | 2 | 2041-2043 | |
| 71 | Enrique Sandoval | 2 | 2035-2036 | |
| 71 | Brent Torres | 2 | 2043-2043 | |
| 71 | Gary Veilleux | 2 | 2036-2036 | |
| 91 | Geordie Adams# | 1 | 2051-2051 | |
| 91 | Ryan Anderson | 1 | 2047-2047 | |
| 91 | Danny Beck | 1 | 2050-2050 | |
| 91 | Lance Blake# | 1 | 2051-2051 | |
| 91 | Joe Braun | 1 | 2036-2036 | |
| 91 | Kyle Brown# | 1 | 2051-2051 | |
| 91 | Omar Chavez | 1 | 2034-2035 | |
| 91 | David Eisert# | 1 | 2049-2049 | |
| 91 | Arturo Espejo | 1 | 2040-2043 | |
| 91 | Alex Gomez# | 1 | 2045-2047 |
