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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Hector Ramirez# | 104 | 2056-2065 | |
| 1 | Paco Vargas | 104 | 2050-2062 | |
| 3 | Noah Whitehead# | 98 | 2053-2063 | |
| 4 | Cooper Pence# | 97 | 2054-2063 | |
| 5 | Clay Wilson# | 92 | 2049-2064 | |
| 6 | Damian Phillips# | 86 | 2059-2064 | |
| 7 | Nathan Rogers# | 79 | 2051-2065 | |
| 8 | Diego Rodriguez | 75 | 2019-2030 | |
| 9 | Jermaine Dodson | 72 | 2026-2034 | |
| 10 | Cary Hall# | 70 | 2054-2063 | |
| 10 | Sancho Rivera# | 70 | 2056-2065 | |
| 12 | Jaime Flores# | 68 | 2058-2065 | |
| 12 | Brennan Powell# | 68 | 2059-2065 | |
| 14 | Don Miller# | 67 | 2056-2065 | |
| 15 | Will Atkins# | 65 | 2056-2064 | |
| 15 | Jose Mercado | 65 | 2041-2048 | |
| 17 | Reynaldo Martinez# | 63 | 2057-2065 | |
| 17 | Nobuyori Yamashita# | 63 | 2058-2065 | |
| 19 | Adrian Wells# | 62 | 2059-2065 | |
| 20 | Clemente Encarnacion# | 61 | 2052-2065 | |
| 21 | Jeff Moore | 60 | 2048-2056 | |
| 22 | Chris Rosa# | 58 | 2058-2065 | |
| 23 | Jason Arnold# | 56 | 2053-2064 | |
| 23 | Mark Wall# | 56 | 2059-2065 | |
| 25 | Jose Estrada | 55 | 2025-2034 | |
| 25 | Anastasio Guevara# | 55 | 2060-2065 | |
| 27 | Dennis Diaz# | 54 | 2056-2065 | |
| 27 | Vernon Gray# | 54 | 2057-2065 | |
| 27 | Norman Lund# | 54 | 2056-2065 | |
| 27 | Felix Perez# | 54 | 2059-2065 | |
| 27 | Joseph Sullivan# | 54 | 2060-2065 | |
| 32 | Enrico Garcia# | 52 | 2049-2063 | |
| 32 | Owen Phelps# | 52 | 2057-2064 | |
| 34 | Roderick Dougan | 51 | 2028-2032 | |
| 34 | Vincente Pacheco | 51 | 2020-2025 | |
| 34 | Flint Tidmarch# | 51 | 2058-2065 | |
| 34 | William Williams# | 51 | 2055-2063 | |
| 38 | Aurelio Corona# | 50 | 2061-2065 | |
| 38 | Carlos Martinez# | 50 | 2059-2065 | |
| 38 | Tucker Slater# | 50 | 2057-2065 | |
| 41 | Doug Cansler# | 49 | 2060-2065 | |
| 42 | Cisco Aquino | 48 | 2019-2030 | |
| 42 | Mario Espinoza | 48 | 2022-2030 | |
| 42 | Rick Moran# | 48 | 2059-2064 | |
| 42 | Chip Wiley# | 48 | 2061-2065 | |
| 46 | Julio Alvarado | 47 | 2022-2035 | |
| 46 | Cory Nixon | 47 | 2028-2035 | |
| 46 | Bradley Shepherd# | 47 | 2060-2065 | |
| 46 | Denny Wilson# | 47 | 2057-2064 | |
| 50 | Arthur Clark | 46 | 2022-2030 | |
| 50 | Harry Dickerson | 46 | 2048-2055 | |
| 52 | Nathan Beechey# | 45 | 2060-2065 | |
| 52 | Norbert Leonard# | 45 | 2058-2063 | |
| 52 | Allen Lloyd# | 45 | 2053-2065 | |
| 52 | Julius Lyons | 45 | 2021-2031 | |
| 52 | Gary Thomas# | 45 | 2059-2065 | |
| 57 | Michael Elliott | 44 | 2026-2030 | |
| 57 | Kelly Franklin | 44 | 2045-2059 | |
| 57 | Gerald Holloway# | 44 | 2057-2064 | |
| 57 | Steve Stafford# | 44 | 2056-2065 | |
| 57 | Matt Wilder# | 44 | 2061-2065 | |
| 62 | Tom Avalos# | 43 | 2052-2063 | |
| 62 | Luis Bernal# | 43 | 2061-2065 | |
| 62 | Manuel Garcia# | 43 | 2056-2065 | |
| 62 | Colm Goode# | 43 | 2060-2063 | |
| 62 | Stu Hunter# | 43 | 2058-2065 | |
| 67 | Dale Brown# | 42 | 2057-2060 | |
| 67 | Keith Hinkle# | 42 | 2054-2057 | |
| 67 | Miguel Luna# | 42 | 2058-2063 | |
| 67 | Dan McCann# | 42 | 2054-2064 | |
| 67 | David Ramos# | 42 | 2058-2061 | |
| 67 | Dale Walker | 42 | 2021-2031 | |
| 73 | Eugene Gonzalez | 41 | 2048-2055 | |
| 73 | Arthur Howard# | 41 | 2055-2058 | |
| 73 | Ed Lee# | 41 | 2059-2065 | |
| 73 | Francisco Ortiz# | 41 | 2057-2065 | |
| 73 | Juan Rivera | 41 | 2019-2026 | |
| 73 | Ryan Sanders# | 41 | 2058-2065 | |
| 73 | Kyle Sherman# | 41 | 2059-2064 | |
| 80 | Brandon Battle | 40 | 2019-2032 | |
| 80 | David Herbert | 40 | 2052-2060 | |
| 80 | Vicente Maldonado | 40 | 2020-2029 | |
| 80 | Elijah Wall | 40 | 2046-2059 | |
| 80 | Mike Williams | 40 | 2049-2061 | |
| 85 | Sean Barrett | 39 | 2034-2047 | |
| 85 | Jose Cruz# | 39 | 2060-2063 | |
| 85 | Robert Dawson | 39 | 2019-2026 | |
| 85 | Albert Flores# | 39 | 2057-2061 | |
| 85 | Leonardo Morales | 39 | 2049-2052 | |
| 85 | Scott Rhodes# | 39 | 2061-2065 | |
| 85 | Antonio Rivera# | 39 | 2058-2062 | |
| 85 | Tim Rocha# | 39 | 2061-2065 | |
| 85 | Julius Ward# | 39 | 2053-2063 | |
| 85 | Leon Webster# | 39 | 2056-2065 | |
| 85 | Ryan Wilkinson# | 39 | 2055-2065 | |
| 96 | Robbie Caldwell# | 38 | 2057-2060 | |
| 96 | Tony Hernandez# | 38 | 2058-2063 | |
| 96 | Steve Hubbard | 38 | 2052-2063 | |
| 96 | Alvin Skinner# | 38 | 2059-2065 | |
| 100 | Carlos Ayala | 37 | 2019-2025 |
