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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Kareem Brobbey* | 256 | 2024-2046 | |
| 2 | Mike Clark* | 244 | 2028-2047 | |
| 3 | Dave Smith* | 222 | 2024-2046 | |
| 4 | Luis Salazar* | 211 | 2024-2044 | |
| 5 | Stephen Wilkins* | 208 | 2024-2045 | |
| 6 | Mario Villalobos | 207 | 2024-2044 | |
| 7 | Ruben Sanchez* | 200 | 2024-2045 | |
| 8 | Josh Neal* | 197 | 2030-2049 | |
| 9 | Willie de Leon* | 192 | 2024-2038 | |
| 9 | Brett Skinner# | 192 | 2034-2055 | |
| 11 | Travis Welker | 185 | 2024-2045 | |
| 12 | Jorge Rodriquez* | 174 | 2024-2043 | |
| 13 | Colin Denman | 173 | 2024-2043 | |
| 14 | Carlos Juarez* | 172 | 2024-2043 | |
| 15 | Edgar Villagomez | 171 | 2024-2043 | |
| 16 | Greg Olsen | 168 | 2027-2043 | |
| 17 | Benjamin Lecomte* | 165 | 2032-2050 | |
| 18 | Juan Magana# | 163 | 2042-2055 | |
| 19 | David Melchor# | 162 | 2039-2055 | |
| 20 | Danny Gephart* | 161 | 2024-2045 | |
| 21 | Corey Gillis* | 157 | 2024-2039 | |
| 22 | Chris Carrell | 154 | 2028-2046 | |
| 23 | Mitch Burgess | 150 | 2024-2040 | |
| 24 | Ernesto Duarte# | 146 | 2044-2055 | |
| 24 | Russell Schneider# | 146 | 2040-2055 | |
| 26 | Victor Sandoval | 144 | 2024-2042 | |
| 27 | Vic Marinez# | 141 | 2041-2055 | |
| 27 | Pedro Ochoa# | 141 | 2041-2055 | |
| 29 | Mario Villalpando | 139 | 2024-2042 | |
| 30 | Jake Price# | 137 | 2044-2055 | |
| 31 | Tom Parker | 134 | 2024-2043 | |
| 32 | J.P. Lutz | 130 | 2033-2050 | |
| 33 | Malachi Brock# | 127 | 2041-2055 | |
| 33 | Vicente Santiago# | 127 | 2043-2055 | |
| 35 | Jon Cornejo | 126 | 2024-2041 | |
| 35 | Andy Partlow# | 126 | 2043-2055 | |
| 35 | Luis Vega# | 126 | 2043-2055 | |
| 38 | Mitch Kroening# | 122 | 2043-2055 | |
| 39 | Alex Sanchez | 121 | 2028-2045 | |
| 40 | Ron Martin | 120 | 2032-2046 | |
| 41 | Mike White | 118 | 2035-2050 | |
| 42 | Matt Player* | 116 | 2024-2037 | |
| 43 | Mario Chaidez | 114 | 2024-2040 | |
| 43 | Nick Sorensen | 114 | 2024-2041 | |
| 45 | Rémy Girard | 113 | 2024-2043 | |
| 46 | Josh Davis | 111 | 2028-2040 | |
| 46 | Matt Harris | 111 | 2027-2042 | |
| 48 | Andrew Mabry | 110 | 2024-2040 | |
| 49 | Justin Brussow | 109 | 2035-2048 | |
| 49 | Luis Moreno# | 109 | 2046-2055 | |
| 51 | Alfonso Garbiso# | 108 | 2042-2055 | |
| 52 | Ramon Betancourt* | 107 | 2024-2048 | |
| 52 | Miguel Rivera | 107 | 2024-2037 | |
| 54 | Bobby Juarez | 106 | 2024-2037 | |
| 55 | Luis Calderon | 103 | 2036-2048 | |
| 55 | Adam Thompson | 103 | 2029-2046 | |
| 57 | Mikael Bonin | 102 | 2032-2046 | |
| 57 | Tim Rose | 102 | 2024-2040 | |
| 59 | Nestor Perez | 101 | 2024-2037 | |
| 60 | Joe Fenton | 100 | 2030-2046 | |
| 60 | Angelo Pulido | 100 | 2035-2046 | |
| 62 | Ricky Acosta | 98 | 2024-2040 | |
| 62 | Mike Beltran | 98 | 2032-2044 | |
| 62 | Jaden Reddicks | 98 | 2038-2052 | |
| 62 | Aaron Staff | 98 | 2024-2036 | |
| 66 | Miguel Millan | 96 | 2036-2047 | |
| 67 | Ian Rowland# | 95 | 2043-2055 | |
| 68 | Ricardo Davalos | 94 | 2032-2044 | |
| 69 | Carlos Becerra# | 93 | 2046-2055 | |
| 70 | Raul Rodriguez# | 92 | 2042-2051 | |
| 70 | Pat Rudd | 92 | 2033-2045 | |
| 72 | Yan Lopez | 91 | 2024-2043 | |
| 73 | Rico Duran | 89 | 2024-2036 | |
| 73 | Andy Urso* | 89 | 2024-2046 | |
| 75 | Marcos Aldaco* | 88 | 2024-2049 | |
| 75 | Gerardo Cantu | 88 | 2030-2041 | |
| 75 | Roy Ogorek# | 88 | 2044-2055 | |
| 78 | Robert Medina | 87 | 2028-2046 | |
| 78 | Josh Thorp | 87 | 2024-2039 | |
| 78 | Steve Van Orsdol# | 87 | 2045-2055 | |
| 81 | Bobby Araujo# | 86 | 2045-2055 | |
| 81 | Bill Kowalchuk | 86 | 2024-2044 | |
| 81 | Angel Lopez | 86 | 2024-2038 | |
| 81 | Alex Matos# | 86 | 2045-2055 | |
| 81 | Arturo Paredes | 86 | 2024-2039 | |
| 86 | Matt Gardner | 84 | 2024-2037 | |
| 86 | Ryan Kimball | 84 | 2029-2043 | |
| 88 | Lance Daniello | 83 | 2040-2052 | |
| 88 | Gary Gunnoe | 83 | 2024-2046 | |
| 90 | Jesus Alaniz | 82 | 2025-2039 | |
| 90 | Frank Ordonez# | 82 | 2048-2055 | |
| 90 | Danny Ramirez# | 82 | 2042-2055 | |
| 93 | Tony Alba* | 80 | 2030-2050 | |
| 93 | Juan Rosario# | 80 | 2043-2055 | |
| 95 | Rich Cole | 79 | 2029-2042 | |
| 95 | Felix Hernandez | 79 | 2024-2039 | |
| 95 | Edgar Rodriguez | 79 | 2040-2051 | |
| 98 | Harry Landers | 78 | 2024-2040 | |
| 99 | John Allison | 77 | 2024-2041 | |
| 99 | Bob Figueroa | 77 | 2037-2048 |
