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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 | Brad Sleezer# | 6 | 2050-2050 | |
| 25 | Edwin Esquivel | 5 | 2047-2047 | |
| 25 | Jose Garcia | 5 | 2035-2037 | |
| 25 | Bill Guyett | 5 | 2041-2043 | |
| 25 | Jim Herrick | 5 | 2038-2038 | |
| 25 | Eric O'Hara | 5 | 2048-2048 | |
| 25 | Corey Palmer | 5 | 2034-2035 | |
| 25 | Jeff Rabinowitz# | 5 | 2045-2045 | |
| 25 | Miguel Rios# | 5 | 2048-2048 | |
| 25 | Tyler Robinson# | 5 | 2051-2051 | |
| 25 | Santiago Robles | 5 | 2045-2045 | |
| 25 | Ricardo Rossito | 5 | 2038-2038 | |
| 25 | Chris Shewey# | 5 | 2049-2049 | |
| 25 | Nick Taylor# | 5 | 2051-2051 | |
| 25 | Jason Thomas | 5 | 2045-2045 | |
| 25 | Ruben Torres | 5 | 2044-2044 | |
| 25 | Braxton Wallace | 5 | 2044-2044 | |
| 41 | Alberto Aranda | 4 | 2033-2033 | |
| 41 | Adam Brown | 4 | 2037-2037 | |
| 41 | Alex Camarillo | 4 | 2048-2048 | |
| 41 | Kurat Feyzioglu# | 4 | 2034-2042 | |
| 41 | Brett Gross | 4 | 2034-2034 | |
| 41 | Ricky Hernandez | 4 | 2041-2041 | |
| 41 | Miguel Leon | 4 | 2034-2034 | |
| 41 | Doug Maag | 4 | 2046-2046 | |
| 41 | David Madden# | 4 | 2051-2051 | |
| 41 | Jon Orozco | 4 | 2046-2046 | |
| 41 | Tony Perez# | 4 | 2051-2051 | |
| 41 | Nelson Ramos | 4 | 2033-2033 | |
| 41 | Kevin Renninger | 4 | 2038-2038 | |
| 41 | Bryan Rice# | 4 | 2051-2051 | |
| 41 | Ben Schuman# | 4 | 2051-2051 | |
| 41 | Josh Semmons# | 4 | 2051-2051 | |
| 41 | Curtis Weidman | 4 | 2035-2035 | |
| 58 | Chris Adams | 3 | 2048-2048 | |
| 58 | Ira Aguilar | 3 | 2034-2034 | |
| 58 | Wayne Ayler | 3 | 2033-2033 | |
| 58 | Sean Beshear# | 3 | 2051-2051 | |
| 58 | Chad Britt | 3 | 2032-2032 | |
| 58 | Quadir Brown# | 3 | 2048-2050 | |
| 58 | Willie Colon# | 3 | 2051-2051 | |
| 58 | Tommy Esparza | 3 | 2033-2033 | |
| 58 | Omar Garcia | 3 | 2036-2037 | |
| 58 | Zeke Hernandez | 3 | 2040-2044 | |
| 58 | Mauricio Herrera | 3 | 2035-2035 | |
| 58 | Randy Letson | 3 | 2036-2043 | |
| 58 | Ken Mason | 3 | 2049-2050 | |
| 58 | Josh McMahon | 3 | 2033-2037 | |
| 58 | Mike Nichols# | 3 | 2051-2051 | |
| 58 | Bryant Patterson | 3 | 2042-2042 | |
| 58 | Joey Roberts | 3 | 2037-2037 | |
| 58 | Francisco Rodriguez | 3 | 2036-2036 | |
| 58 | Edgar Torres | 3 | 2034-2034 | |
| 77 | Adam Auger# | 2 | 2049-2049 | |
| 77 | Wilson Ballinas | 2 | 2039-2040 | |
| 77 | Flinn Berthelsen | 2 | 2039-2043 | |
| 77 | Michael Boling# | 2 | 2051-2051 | |
| 77 | Chris Castilleja# | 2 | 2051-2051 | |
| 77 | Matt Causey | 2 | 2033-2033 | |
| 77 | Enrique Giraldo | 2 | 2039-2041 | |
| 77 | Chandler Grice | 2 | 2047-2048 | |
| 77 | Alex Harper# | 2 | 2048-2049 | |
| 77 | Alex Huertas | 2 | 2038-2040 | |
| 77 | Logan Itterly | 2 | 2042-2042 | |
| 77 | Pedro Lopez# | 2 | 2049-2049 | |
| 77 | Rogelio Lopez | 2 | 2047-2047 | |
| 77 | Arturo Mancera | 2 | 2042-2043 | |
| 77 | Jarred Mann | 2 | 2035-2035 | |
| 77 | Chris Marr# | 2 | 2051-2051 | |
| 77 | Mike Matter | 2 | 2033-2033 | |
| 77 | C.J. Miles# | 2 | 2051-2051 | |
| 77 | Gaetan Noe | 2 | 2043-2043 | |
| 77 | Adam O'Rourke | 2 | 2034-2034 | |
| 77 | Josh Plum# | 2 | 2051-2051 | |
| 77 | Joe Rice | 2 | 2041-2043 | |
| 77 | Enrique Sandoval | 2 | 2035-2036 | |
| 77 | Chris Schlichting# | 2 | 2051-2051 |
