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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Kareem Brobbey# | 247 | 2024-2045 | |
| 2 | Mike Clark# | 232 | 2028-2045 | |
| 3 | Dave Smith# | 213 | 2024-2045 | |
| 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 | Willie de Leon* | 192 | 2024-2038 | |
| 9 | Travis Welker | 185 | 2024-2045 | |
| 10 | Jorge Rodriquez | 174 | 2024-2043 | |
| 11 | Colin Denman | 173 | 2024-2043 | |
| 12 | Carlos Juarez | 172 | 2024-2043 | |
| 12 | Josh Neal# | 172 | 2030-2045 | |
| 14 | Edgar Villagomez | 171 | 2024-2043 | |
| 15 | Greg Olsen | 168 | 2027-2043 | |
| 16 | Danny Gephart | 161 | 2024-2045 | |
| 17 | Corey Gillis* | 157 | 2024-2039 | |
| 18 | Chris Carrell# | 153 | 2028-2045 | |
| 19 | Mitch Burgess | 150 | 2024-2040 | |
| 20 | Victor Sandoval | 144 | 2024-2042 | |
| 21 | Mario Villalpando | 139 | 2024-2042 | |
| 22 | Benjamin Lecomte# | 138 | 2032-2045 | |
| 23 | Tom Parker | 134 | 2024-2043 | |
| 24 | Jon Cornejo | 126 | 2024-2041 | |
| 25 | Alex Sanchez | 121 | 2028-2045 | |
| 26 | Ron Martin# | 119 | 2032-2045 | |
| 27 | Matt Player* | 116 | 2024-2037 | |
| 28 | Mario Chaidez | 114 | 2024-2040 | |
| 28 | Nick Sorensen | 114 | 2024-2041 | |
| 30 | Rémy Girard | 113 | 2024-2043 | |
| 31 | J.P. Lutz# | 112 | 2033-2045 | |
| 32 | Josh Davis | 111 | 2028-2040 | |
| 32 | Matt Harris | 111 | 2027-2042 | |
| 34 | Andrew Mabry | 110 | 2024-2040 | |
| 35 | Miguel Rivera | 107 | 2024-2037 | |
| 36 | Bobby Juarez | 106 | 2024-2037 | |
| 37 | Justin Brussow# | 104 | 2035-2045 | |
| 38 | Tim Rose | 102 | 2024-2040 | |
| 39 | Nestor Perez | 101 | 2024-2037 | |
| 39 | Adam Thompson# | 101 | 2029-2045 | |
| 41 | Mikael Bonin# | 100 | 2032-2045 | |
| 42 | Joe Fenton# | 99 | 2030-2044 | |
| 43 | Ricky Acosta | 98 | 2024-2040 | |
| 43 | Mike Beltran | 98 | 2032-2044 | |
| 43 | Angelo Pulido# | 98 | 2035-2045 | |
| 43 | Aaron Staff | 98 | 2024-2036 | |
| 47 | Ramon Betancourt# | 97 | 2024-2045 | |
| 47 | Brett Skinner# | 97 | 2034-2045 | |
| 47 | Mike White# | 97 | 2035-2045 | |
| 50 | Ricardo Davalos | 94 | 2032-2044 | |
| 51 | Luis Calderon# | 92 | 2036-2045 | |
| 51 | Pat Rudd# | 92 | 2033-2045 | |
| 53 | Yan Lopez | 91 | 2024-2043 | |
| 54 | Rico Duran | 89 | 2024-2036 | |
| 54 | Andy Urso# | 89 | 2024-2045 | |
| 56 | Gerardo Cantu | 88 | 2030-2041 | |
| 57 | Robert Medina# | 87 | 2028-2045 | |
| 57 | Josh Thorp | 87 | 2024-2039 | |
| 59 | Bill Kowalchuk | 86 | 2024-2044 | |
| 59 | Angel Lopez | 86 | 2024-2038 | |
| 59 | Arturo Paredes | 86 | 2024-2039 | |
| 62 | Matt Gardner | 84 | 2024-2037 | |
| 62 | Ryan Kimball | 84 | 2029-2043 | |
| 62 | Miguel Millan# | 84 | 2036-2045 | |
| 65 | Jesus Alaniz | 82 | 2025-2039 | |
| 66 | Rich Cole | 79 | 2029-2042 | |
| 66 | Gary Gunnoe# | 79 | 2024-2045 | |
| 66 | Felix Hernandez | 79 | 2024-2039 | |
| 69 | Harry Landers | 78 | 2024-2040 | |
| 70 | John Allison | 77 | 2024-2041 | |
| 70 | Adam Herman | 77 | 2028-2041 | |
| 70 | Phil Racine | 77 | 2024-2037 | |
| 70 | David Zeits | 77 | 2028-2042 | |
| 74 | Marcos Aldaco# | 76 | 2024-2045 | |
| 74 | Shan-bo Li | 76 | 2024-2037 | |
| 74 | Roberto Valladarez | 76 | 2032-2045 | |
| 77 | David Melchor# | 75 | 2039-2045 | |
| 78 | German Guajardo | 73 | 2025-2041 | |
| 78 | Joel Tangarife | 73 | 2024-2036 | |
| 80 | Tony Alba# | 72 | 2030-2045 | |
| 80 | Ben Moore | 72 | 2024-2034 | |
| 82 | Derrick Hightower | 71 | 2024-2037 | |
| 82 | Matt Jennings# | 71 | 2035-2045 | |
| 82 | Scott Kelly | 71 | 2024-2045 | |
| 82 | Alex Ramirez# | 71 | 2024-2045 | |
| 82 | Angelo Trevino# | 71 | 2037-2045 | |
| 87 | Steve Tyler | 70 | 2024-2042 | |
| 88 | Tim Lugo | 69 | 2024-2035 | |
| 88 | Roberto Vivanco | 69 | 2035-2045 | |
| 90 | Willie Ayala | 68 | 2024-2042 | |
| 90 | Travis Segura# | 68 | 2035-2045 | |
| 92 | Fumitoshi Fujiwara | 67 | 2028-2041 | |
| 92 | Jason Nicolich | 67 | 2024-2031 | |
| 94 | Jeff Bolser# | 66 | 2035-2045 | |
| 95 | John Pilkington# | 65 | 2024-2045 | |
| 96 | Casey Basler | 64 | 2024-2042 | |
| 96 | Dave Kellermann# | 64 | 2032-2045 | |
| 96 | Bryan Kesling | 64 | 2024-2036 | |
| 96 | Leo Marquez | 64 | 2024-2037 | |
| 96 | Mauk van den Biggelaar | 64 | 2024-2045 |
