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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Ben Kitch# | 14 | 2047-2048 | |
| 2 | Jerry Matthews# | 13 | 2035-2040 | |
| 3 | Brian Christian | 12 | 2035-2043 | |
| 3 | T.J. Johnson | 12 | 2040-2042 | |
| 5 | Justin Gray# | 10 | 2046-2048 | |
| 5 | Juan Rodriguez | 10 | 2040-2043 | |
| 7 | Mark Vecchio | 9 | 2036-2043 | |
| 8 | Ricky Arriola | 8 | 2039-2042 | |
| 8 | Mario Marin | 8 | 2041-2043 | |
| 10 | Calvin Birley# | 7 | 2045-2045 | |
| 10 | Josh Conway | 7 | 2038-2040 | |
| 10 | Ben Peter | 7 | 2035-2036 | |
| 13 | Fernando Alvarez | 6 | 2044-2044 | |
| 13 | Alberto Camacho | 6 | 2043-2044 | |
| 13 | Jorge de la Torre# | 6 | 2046-2046 | |
| 13 | Ben Exley | 6 | 2039-2041 | |
| 13 | Tony Fernandez# | 6 | 2046-2046 | |
| 13 | Tom Markee | 6 | 2045-2045 | |
| 19 | Edwin Esquivel# | 5 | 2047-2047 | |
| 19 | Jose Garcia | 5 | 2035-2037 | |
| 19 | Bill Guyett | 5 | 2041-2043 | |
| 19 | Jim Herrick | 5 | 2038-2038 | |
| 19 | Eric O'Hara# | 5 | 2048-2048 | |
| 19 | Corey Palmer | 5 | 2034-2035 | |
| 19 | Jeff Rabinowitz# | 5 | 2045-2045 | |
| 19 | Miguel Rios# | 5 | 2048-2048 | |
| 19 | Santiago Robles | 5 | 2045-2045 | |
| 19 | Matt Rockmore# | 5 | 2048-2049 | |
| 19 | Yakir Roman# | 5 | 2049-2049 | |
| 19 | Ricardo Rossito | 5 | 2038-2038 | |
| 19 | Chris Shewey# | 5 | 2049-2049 | |
| 19 | Jason Thomas# | 5 | 2045-2045 | |
| 19 | Ruben Torres | 5 | 2044-2044 | |
| 19 | Braxton Wallace | 5 | 2044-2044 | |
| 35 | Alberto Aranda | 4 | 2033-2033 | |
| 35 | Adam Brown | 4 | 2037-2037 | |
| 35 | Alex Camarillo# | 4 | 2048-2048 | |
| 35 | Kurat Feyzioglu# | 4 | 2034-2042 | |
| 35 | Brett Gross | 4 | 2034-2034 | |
| 35 | Ricky Hernandez# | 4 | 2041-2041 | |
| 35 | Miguel Leon | 4 | 2034-2034 | |
| 35 | Doug Maag | 4 | 2046-2046 | |
| 35 | Jon Orozco# | 4 | 2046-2046 | |
| 35 | Matt Poole# | 4 | 2049-2049 | |
| 35 | Nelson Ramos | 4 | 2033-2033 | |
| 35 | Kevin Renninger | 4 | 2038-2038 | |
| 35 | Curtis Weidman | 4 | 2035-2035 | |
| 48 | Chris Adams# | 3 | 2048-2048 | |
| 48 | Ira Aguilar | 3 | 2034-2034 | |
| 48 | Wayne Ayler | 3 | 2033-2033 | |
| 48 | Chad Britt | 3 | 2032-2032 | |
| 48 | Tommy Esparza | 3 | 2033-2033 | |
| 48 | Omar Garcia | 3 | 2036-2037 | |
| 48 | Zeke Hernandez# | 3 | 2040-2044 | |
| 48 | Mauricio Herrera | 3 | 2035-2035 | |
| 48 | Randy Letson | 3 | 2036-2043 | |
| 48 | Ken Mason# | 3 | 2049-2049 | |
| 48 | Josh McMahon | 3 | 2033-2037 | |
| 48 | Bryant Patterson | 3 | 2042-2042 | |
| 48 | Joey Roberts | 3 | 2037-2037 | |
| 48 | Francisco Rodriguez | 3 | 2036-2036 | |
| 48 | Edgar Torres | 3 | 2034-2034 | |
| 63 | Adam Auger# | 2 | 2049-2049 | |
| 63 | Wilson Ballinas | 2 | 2039-2040 | |
| 63 | Flinn Berthelsen | 2 | 2039-2043 | |
| 63 | Quadir Brown# | 2 | 2048-2049 | |
| 63 | Matt Causey | 2 | 2033-2033 | |
| 63 | Enrique Giraldo | 2 | 2039-2041 | |
| 63 | Chandler Grice# | 2 | 2047-2048 | |
| 63 | Alex Harper# | 2 | 2048-2049 | |
| 63 | Alex Huertas | 2 | 2038-2040 | |
| 63 | Logan Itterly | 2 | 2042-2042 | |
| 63 | Pedro Lopez# | 2 | 2049-2049 | |
| 63 | Rogelio Lopez# | 2 | 2047-2047 | |
| 63 | Arturo Mancera | 2 | 2042-2043 | |
| 63 | Jarred Mann | 2 | 2035-2035 | |
| 63 | Mike Matter | 2 | 2033-2033 | |
| 63 | Gaetan Noe | 2 | 2043-2043 | |
| 63 | Adam O'Rourke | 2 | 2034-2034 | |
| 63 | Joe Rice | 2 | 2041-2043 | |
| 63 | Enrique Sandoval | 2 | 2035-2036 | |
| 63 | Brent Torres | 2 | 2043-2043 | |
| 63 | Gary Veilleux | 2 | 2036-2036 | |
| 84 | Ryan Anderson | 1 | 2047-2047 | |
| 84 | Joe Braun# | 1 | 2036-2036 | |
| 84 | Omar Chavez | 1 | 2034-2035 | |
| 84 | David Eisert# | 1 | 2049-2049 | |
| 84 | Arturo Espejo | 1 | 2040-2043 | |
| 84 | Alex Gomez# | 1 | 2045-2047 | |
| 84 | Chi-hyeon Jang | 1 | 2041-2041 | |
| 84 | Cameron Keller | 1 | 2045-2045 | |
| 84 | Jim Lynn | 1 | 2047-2047 | |
| 84 | Rafael Marin | 1 | 2034-2034 | |
| 84 | Ken McCombs# | 1 | 2044-2044 | |
| 84 | Bill Muscott | 1 | 2037-2037 | |
| 84 | Nick Northrup | 1 | 2046-2046 | |
| 84 | Rich Richmond | 1 | 2038-2038 | |
| 84 | Paul Rigney | 1 | 2046-2047 | |
| 84 | William Rodriguez# | 1 | 2046-2047 | |
| 84 | Dan Rogers# | 1 | 2048-2049 |
