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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Alex Castaneda | 68 | 2023-2029 | |
| 2 | Horace Wilder | 67 | 2030-2037 | |
| 3 | Jackson Gephart | 57 | 2039-2043 | |
| 4 | Logan Hamlin | 55 | 2035-2040 | |
| 4 | Jimmy Richards | 55 | 2021-2025 | |
| 6 | Juan Camargo | 53 | 2004-2011 | |
| 7 | Matt Clark# | 52 | 2047-2050 | |
| 7 | Ryker Moss | 52 | 2035-2040 | |
| 9 | Adam Crosby | 51 | 2009-2012 | |
| 10 | Danny Denton | 50 | 2019-2023 | |
| 10 | Rush Harvey | 50 | 2036-2044 | |
| 12 | John Allen | 49 | 2025-2030 | |
| 12 | Danny Newlin | 49 | 2014-2020 | |
| 14 | Joe Maluchnik | 48 | 2026-2032 | |
| 15 | Cy Philippi | 47 | 2035-2041 | |
| 15 | Mike Stephens | 47 | 2010-2014 | |
| 17 | Tex Durham | 46 | 2038-2043 | |
| 17 | Alexis Hernandez | 46 | 2024-2027 | |
| 17 | Shawn Moffitt | 46 | 2034-2039 | |
| 20 | Bobby Emerson | 45 | 2010-2014 | |
| 20 | Willie Estrada | 45 | 2016-2019 | |
| 22 | Chad Castelano | 44 | 2035-2039 | |
| 22 | K.J. Stonge# | 44 | 2044-2047 | |
| 24 | Tom Dunifer | 43 | 2006-2011 | |
| 24 | Jerry Moran | 43 | 2028-2033 | |
| 24 | John Pimentel# | 43 | 2043-2047 | |
| 24 | Warren Richards | 43 | 2033-2038 | |
| 24 | Forster Stevens | 43 | 2039-2045 | |
| 29 | Alvaro Barajas | 42 | 2022-2027 | |
| 29 | Corey Bethea | 42 | 2027-2031 | |
| 29 | Ron Brenke | 42 | 2011-2015 | |
| 29 | Dave de Burgh# | 42 | 2044-2047 | |
| 29 | Alfredo Martín# | 42 | 2041-2045 | |
| 29 | Gerardo Solis | 42 | 2010-2014 | |
| 35 | Iggy Canchola# | 41 | 2047-2050 | |
| 35 | Omar Cativo | 41 | 2025-2029 | |
| 35 | Mateo Cruz# | 41 | 2041-2045 | |
| 35 | Gabe Dunlap | 41 | 2024-2028 | |
| 35 | Lupe Galan | 41 | 2012-2017 | |
| 35 | Tyler Hyatt | 41 | 2030-2035 | |
| 35 | David Martinez | 41 | 2007-2014 | |
| 35 | Kent Michael# | 41 | 2047-2050 | |
| 35 | Rogelio Orta | 41 | 2005-2010 | |
| 44 | Derek Boger# | 40 | 2042-2045 | |
| 44 | Danny de Jesus | 40 | 2019-2024 | |
| 44 | Adam Knight | 40 | 2013-2018 | |
| 44 | Eric Meade | 40 | 2020-2023 | |
| 44 | Bayron Romero | 40 | 2039-2042 | |
| 49 | Stephon Canada | 39 | 2004-2008 | |
| 49 | Raul Casas | 39 | 2021-2025 | |
| 49 | Stan Harris# | 39 | 2043-2047 | |
| 49 | Horado Luque | 39 | 2005-2009 | |
| 49 | T.J. Picchione# | 39 | 2046-2050 | |
| 49 | Jorge Salazar | 39 | 2004-2007 | |
| 49 | Jorge Saldana | 39 | 2006-2011 | |
| 49 | Juan Sanchez | 39 | 2022-2028 | |
| 49 | Fernando Santiago | 39 | 2013-2016 | |
| 49 | David Stewart | 39 | 2027-2033 | |
| 49 | Danny Valdez | 39 | 2020-2025 | |
| 49 | Chris Wilson | 39 | 2028-2033 | |
| 61 | John Duncan | 38 | 2033-2038 | |
| 61 | Chris Gauthreaux | 38 | 2028-2034 | |
| 61 | Seymour Lockard | 38 | 2039-2041 | |
| 61 | Robbie Minella | 38 | 2035-2038 | |
| 61 | Luke Redman# | 38 | 2041-2046 | |
| 61 | Raiden Wilson | 38 | 2034-2038 | |
| 67 | Andy Amezcua | 37 | 2011-2016 | |
| 67 | Jack Ballentine | 37 | 2011-2014 | |
| 67 | Jeremy Calabrese# | 37 | 2044-2049 | |
| 67 | Gabe Caldwell | 37 | 2018-2023 | |
| 67 | Armani Fauntroy | 37 | 2004-2009 | |
| 67 | Victor Figueroa | 37 | 2028-2035 | |
| 67 | David Forcum | 37 | 2025-2029 | |
| 67 | Tomohiro Kawata | 37 | 2024-2028 | |
| 67 | Art Kelly | 37 | 2014-2018 | |
| 67 | Justin King | 37 | 2014-2020 | |
| 67 | Tariq Okonkwo | 37 | 2032-2035 | |
| 67 | Jorge Rojas | 37 | 2008-2013 | |
| 67 | Tebaldo Visarrages | 37 | 2038-2040 | |
| 67 | Jonathan Walker | 37 | 2007-2012 | |
| 67 | Monro Witherspoon# | 37 | 2039-2044 | |
| 82 | Ryder Burt# | 36 | 2047-2049 | |
| 82 | Aaron Evans | 36 | 2030-2035 | |
| 82 | Roy Fifield# | 36 | 2045-2049 | |
| 82 | Juan Flores# | 36 | 2036-2040 | |
| 82 | Justin Jackson | 36 | 2030-2034 | |
| 82 | Donovan Keep | 36 | 2043-2048 | |
| 82 | Lourenço Lagos | 36 | 2014-2019 | |
| 82 | Winthrop Merkle | 36 | 2030-2034 | |
| 82 | Dereck Myers | 36 | 2032-2037 | |
| 82 | Cullen O'Neill | 36 | 2035-2038 | |
| 82 | Corey Patton | 36 | 2015-2018 | |
| 82 | Dalbert Reed | 36 | 2036-2041 | |
| 82 | Jacob Rogers | 36 | 2035-2040 | |
| 82 | David Roque | 36 | 2011-2015 | |
| 82 | Arturo Samaripa | 36 | 2007-2012 | |
| 82 | Matt Ward | 36 | 2025-2030 | |
| 82 | Bill Yates | 36 | 2024-2028 | |
| 99 | Dan Green | 35 | 2013-2017 | |
| 99 | Brett Griffie | 35 | 2005-2010 |
