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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Luis Gutierrez | 77 | 2072-2084 | |
| 2 | Orlando Leonardo# | 64 | 2085-2094 | |
| 3 | Josh Erickson | 56 | 2077-2084 | |
| 4 | Bryan Ellis | 47 | 2081-2085 | |
| 5 | Min-yul Kym# | 46 | 2089-2098 | |
| 5 | Rich Romansky | 46 | 2054-2058 | |
| 5 | Brian Williams# | 46 | 2093-2098 | |
| 8 | Matt Dorfman | 43 | 2030-2032 | |
| 9 | Tony Rogue | 42 | 2054-2060 | |
| 10 | Alejandro Alcaraz | 40 | 2067-2074 | |
| 10 | Alex Lozano | 40 | 2084-2096 | |
| 12 | Chris Andraschko | 39 | 2076-2078 | |
| 12 | John Brooke# | 39 | 2095-2097 | |
| 12 | Elias Cruz | 39 | 2090-2094 | |
| 12 | Danny Silva# | 39 | 2088-2091 | |
| 16 | Jamie Doty | 37 | 2053-2056 | |
| 16 | Zach Linginfelter | 37 | 2020-2023 | |
| 18 | Lance Cole# | 36 | 2085-2089 | |
| 18 | Josh Geer | 36 | 2007-2014 | |
| 18 | Bob Manfred | 36 | 2068-2074 | |
| 21 | Andrew Alston | 34 | 2063-2069 | |
| 21 | Chad Emmert | 34 | 2055-2059 | |
| 21 | Allan Gentry# | 34 | 2090-2093 | |
| 21 | Ryan Porterfield# | 34 | 2090-2093 | |
| 25 | Rich Prieto | 33 | 2062-2064 | |
| 26 | Jaden Drayton | 32 | 2056-2059 | |
| 26 | Carlos Felix | 32 | 2018-2023 | |
| 26 | Nick Johnson | 32 | 2051-2052 | |
| 26 | Terry Sabia | 32 | 2086-2090 | |
| 30 | Fernando Aguirre | 31 | 2060-2061 | |
| 30 | Amari Andrews | 31 | 2024-2027 | |
| 30 | Juan Maldonado | 31 | 2065-2078 | |
| 30 | Heriberto Mascarenas | 31 | 2078-2084 | |
| 30 | Tyler Paskewitz | 31 | 2073-2075 | |
| 30 | Angelo Reyes# | 31 | 2092-2098 | |
| 30 | Steve Szetela | 31 | 2079-2092 | |
| 30 | Ossie Valdez | 31 | 2031-2034 | |
| 38 | Chris Ballenger | 30 | 2080-2082 | |
| 38 | Jay Cady | 30 | 2027-2032 | |
| 38 | Josh Klein | 30 | 2090-2091 | |
| 38 | Braden Martin | 30 | 2053-2056 | |
| 38 | Jim Spellman | 30 | 2031-2033 | |
| 43 | Manuel Aguilar | 29 | 2041-2045 | |
| 43 | Paul Blair# | 29 | 2095-2098 | |
| 43 | Wilfredo Casas | 29 | 2083-2084 | |
| 43 | Cody DeRenne | 29 | 2075-2084 | |
| 43 | Rodrigo Munoz | 29 | 2081-2089 | |
| 43 | Josh Sweet | 29 | 2041-2044 | |
| 43 | John Thrailkill# | 29 | 2094-2096 | |
| 43 | Savion Wright# | 29 | 2088-2090 | |
| 51 | Chris Dolcini | 28 | 2077-2080 | |
| 51 | Ryan Farber# | 28 | 2090-2097 | |
| 51 | Nate Hanson | 28 | 2045-2049 | |
| 51 | Alex Obregon | 28 | 2058-2072 | |
| 51 | Steve Rubio | 28 | 2051-2057 | |
| 56 | Alex Bowman | 27 | 2076-2080 | |
| 56 | David Lugo | 27 | 2064-2081 | |
| 56 | Jayden Page | 27 | 2046-2048 | |
| 56 | Pat Potter | 27 | 2082-2084 | |
| 56 | Sam Scelzo# | 27 | 2095-2098 | |
| 56 | Josh Sheeley# | 27 | 2093-2098 | |
| 56 | Felipe Torrijos | 27 | 2083-2084 | |
| 63 | Carlos Bermudez | 26 | 2061-2066 | |
| 63 | Dennis Campion | 26 | 2029-2032 | |
| 63 | Brian Elmore | 26 | 2068-2072 | |
| 63 | John Most | 26 | 2049-2052 | |
| 63 | Michael Murray | 26 | 2017-2020 | |
| 63 | Jose Resto# | 26 | 2094-2098 | |
| 63 | Ivan Zubieta | 26 | 2071-2085 | |
| 70 | Gilberto Archila# | 25 | 2096-2098 | |
| 70 | Travis Blackley | 25 | 2003-2006 | |
| 70 | Kyle Contreras | 25 | 2032-2033 | |
| 70 | Teruyoshi Higashi# | 25 | 2093-2095 | |
| 70 | Dana Miltz | 25 | 2053-2057 | |
| 70 | Carlos Ramos | 25 | 2053-2056 | |
| 70 | Eurico Ratinho | 25 | 2078-2080 | |
| 70 | Ernesto Rodelo | 25 | 2084-2089 | |
| 78 | Eduardo Astudillo# | 24 | 2091-2094 | |
| 78 | Gabe Castle | 24 | 2049-2060 | |
| 78 | Nick Davis | 24 | 2060-2062 | |
| 78 | Joaquin Huerta# | 24 | 2095-2098 | |
| 78 | Rich Raddatz | 24 | 2061-2062 | |
| 78 | Ralph Spiteri# | 24 | 2093-2098 | |
| 84 | Erick Abreu | 23 | 2009-2012 | |
| 84 | Saul Arellano# | 23 | 2093-2095 | |
| 84 | Christian Binford | 23 | 2014-2017 | |
| 84 | Bill Chavez# | 23 | 2092-2095 | |
| 84 | Chase De Jong | 23 | 2016-2019 | |
| 84 | Brad Deppermann | 23 | 2018-2021 | |
| 84 | Ruben Duarte | 23 | 2073-2075 | |
| 84 | Jeremiah Dyke | 23 | 2074-2076 | |
| 84 | Zaire Emmons | 23 | 2068-2071 | |
| 84 | Victor Estrada | 23 | 2053-2065 | |
| 84 | Ismael Giron# | 23 | 2095-2097 | |
| 84 | Rico Lopez | 23 | 2086-2089 | |
| 84 | Angel Martinez | 23 | 2066-2070 | |
| 84 | Curt North | 23 | 2028-2030 | |
| 84 | Antenor Palhares# | 23 | 2095-2097 | |
| 84 | Mark Quick | 23 | 2060-2061 | |
| 84 | Artie Reyes | 23 | 2015-2020 |
