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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Aaron Thornton | 96 | 2040-2052 | |
| 2 | Harrison Hickey | 80 | 2041-2052 | |
| 3 | Edgar Gutierrez | 79 | 2082-2091 | |
| 4 | Ray Timmons | 76 | 2072-2079 | |
| 5 | Jaden Jones | 74 | 2060-2069 | |
| 6 | Shane Bradley | 72 | 2081-2089 | |
| 7 | Tim Krupka | 71 | 2069-2081 | |
| 8 | Mario Trujillo# | 70 | 2089-2098 | |
| 9 | Mike Daley | 69 | 2062-2069 | |
| 9 | Tim Murphy | 69 | 2050-2056 | |
| 9 | Jake Zettel | 69 | 2028-2038 | |
| 12 | Mike Jaffe | 67 | 2031-2038 | |
| 13 | Ed Wiseman# | 66 | 2089-2098 | |
| 14 | Danny Zepeda | 65 | 2065-2076 | |
| 15 | Zaire Stamps | 64 | 2080-2084 | |
| 15 | Mike Stone# | 64 | 2090-2097 | |
| 15 | Hunter Wood | 64 | 2020-2027 | |
| 18 | Jose Bautista | 63 | 2032-2050 | |
| 18 | Frank Hennessy# | 63 | 2089-2096 | |
| 20 | Juan Ruiz | 61 | 2084-2093 | |
| 21 | Michael Shawaryn | 60 | 2018-2027 | |
| 21 | Mike Slayton | 60 | 2040-2048 | |
| 23 | Shawn Bohlen | 59 | 2058-2064 | |
| 23 | Sal Herrera# | 59 | 2090-2096 | |
| 23 | Dallas Kaylor | 59 | 2026-2032 | |
| 23 | Justin Moye# | 59 | 2093-2098 | |
| 27 | Chris Divan | 58 | 2031-2041 | |
| 27 | Matt Rector | 58 | 2077-2084 | |
| 27 | Pete Redd | 58 | 2046-2052 | |
| 30 | Ethan Bailey | 57 | 2069-2074 | |
| 30 | Jonathon Crawford | 57 | 2017-2027 | |
| 30 | Blaine Hardy | 57 | 2013-2023 | |
| 30 | Ben Kramer | 57 | 2044-2054 | |
| 30 | Cody Moore | 57 | 2031-2041 | |
| 30 | Tim Speier | 57 | 2038-2049 | |
| 36 | Willie Estrada | 56 | 2021-2028 | |
| 36 | Kyle Gibson | 56 | 2010-2023 | |
| 36 | Rob Whalen | 56 | 2017-2024 | |
| 39 | Marty Diaz | 55 | 2049-2059 | |
| 39 | Matt Hayden | 55 | 2079-2088 | |
| 39 | Juan Miranda | 55 | 2083-2094 | |
| 39 | Rafael Munoz | 55 | 2046-2053 | |
| 39 | Josh Robbins# | 55 | 2090-2097 | |
| 39 | Erik Verveer | 55 | 2083-2088 | |
| 45 | Brian Castillo | 54 | 2082-2094 | |
| 45 | Arturo Guerra | 54 | 2062-2081 | |
| 45 | Todd Redmond | 54 | 2009-2017 | |
| 48 | Sean Butler | 53 | 2084-2094 | |
| 48 | Naomichi Suzuki | 53 | 2059-2065 | |
| 50 | Eric Brown | 52 | 2038-2046 | |
| 50 | Jonathan Donovan | 52 | 2048-2053 | |
| 50 | Ricardo Garcia | 52 | 2046-2052 | |
| 50 | Alex Gonzalez | 52 | 2061-2077 | |
| 54 | George Bartlett | 51 | 2047-2053 | |
| 54 | Justin Chatham | 51 | 2031-2037 | |
| 54 | Tso-i Chen | 51 | 2026-2031 | |
| 54 | Javier Duque | 51 | 2055-2063 | |
| 54 | Lance Fox | 51 | 2029-2038 | |
| 54 | Pete Gruber | 51 | 2063-2075 | |
| 54 | Butch Kerr | 51 | 2081-2093 | |
| 54 | Ricardo Sauceda# | 51 | 2091-2098 | |
| 62 | Eric DiGiovanni | 50 | 2080-2093 | |
| 62 | Andy Lowman | 50 | 2044-2055 | |
| 62 | Jonas Mexicano | 50 | 2042-2048 | |
| 62 | Clint Salmon | 50 | 2026-2030 | |
| 62 | Jason Young | 50 | 2039-2046 | |
| 67 | Brian Allen | 49 | 2041-2045 | |
| 67 | Ben Bastien | 49 | 2086-2096 | |
| 67 | Edwin Beno | 49 | 2047-2053 | |
| 67 | Jamie Brown | 49 | 2044-2048 | |
| 67 | Jason Castaneda | 49 | 2024-2031 | |
| 67 | Ben Clemons | 49 | 2085-2092 | |
| 67 | Bill Dorsey | 49 | 2024-2033 | |
| 67 | Jerry Flores | 49 | 2083-2089 | |
| 67 | Malik Hill | 49 | 2056-2063 | |
| 67 | Sean Maben | 49 | 2083-2089 | |
| 67 | Rene Ramos | 49 | 2057-2064 | |
| 67 | Edwin Recendiz | 49 | 2033-2041 | |
| 67 | Colin Schwarzrock | 49 | 2076-2083 | |
| 67 | Michael Trulson | 49 | 2077-2082 | |
| 81 | Edgar Brandling | 48 | 2044-2049 | |
| 81 | Mike Dawson | 48 | 2029-2040 | |
| 81 | Garrett Fulenchek | 48 | 2019-2026 | |
| 81 | Matthew Hodge# | 48 | 2093-2097 | |
| 81 | Jaden Wilburn | 48 | 2042-2046 | |
| 86 | Jose Amezquita | 47 | 2050-2062 | |
| 86 | Aurélio Anjinho# | 47 | 2088-2098 | |
| 86 | Nick Bell | 47 | 2077-2081 | |
| 86 | Gabe Canela | 47 | 2022-2030 | |
| 86 | Cesar Corona# | 47 | 2092-2097 | |
| 86 | Ryan Eades | 47 | 2018-2026 | |
| 86 | B.J. Gutierrez# | 47 | 2088-2096 | |
| 86 | Kevin Hanson | 47 | 2047-2055 | |
| 86 | Franklin Lerma | 47 | 2079-2083 | |
| 86 | Alvin Mendez# | 47 | 2092-2098 | |
| 86 | Danny Quintanilla# | 47 | 2085-2098 | |
| 86 | Jesse Reese | 47 | 2046-2052 | |
| 86 | Antonio Sandoval# | 47 | 2088-2093 | |
| 86 | Ismael Santiago | 47 | 2053-2059 | |
| 86 | Kyle Walker | 47 | 2047-2053 |
