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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Juan Villatoro* | 322 | 2009-2026 | |
| 2 | Christopher Hester* | 279 | 2008-2025 | |
| 3 | John Okane* | 277 | 2003-2022 | |
| 4 | Ronald Placencia* | 248 | 2009-2023 | |
| 5 | Enrico Hernández | 244 | 2018-2032 | |
| 6 | Demarcus Ramirez* | 232 | 2002-2018 | |
| 7 | Bruno Talamantez | 229 | 2014-2031 | |
| 8 | Chad Nelligan* | 212 | 2004-2016 | |
| 9 | Fernando Estrada | 205 | 2010-2026 | |
| 10 | Jeffrey Shuttleworth | 202 | 2004-2022 | |
| 11 | Joseph Macaluso | 196 | 2011-2027 | |
| 12 | Ernest Metcalf# | 191 | 2022-2035 | |
| 13 | Chris Williams# | 181 | 2027-2035 | |
| 14 | Donald Hunnicutt | 178 | 2010-2025 | |
| 14 | Toyoshige Takahashi# | 178 | 2025-2035 | |
| 16 | Kevin Kepner | 167 | 2015-2031 | |
| 16 | Frank Osborne | 167 | 2005-2019 | |
| 18 | Isaac Diehl | 166 | 2009-2020 | |
| 18 | Richard Pimental | 166 | 2002-2014 | |
| 20 | William Lawrence | 165 | 2013-2030 | |
| 21 | Erik Moore# | 163 | 2023-2035 | |
| 21 | James Turner | 163 | 2010-2025 | |
| 23 | Albert Garcia | 158 | 2002-2012 | |
| 24 | Yorikane Kichikawa# | 154 | 2024-2035 | |
| 25 | Dennis Durand | 153 | 2012-2025 | |
| 26 | Kyle Fike | 152 | 2010-2024 | |
| 26 | Dario Lopez | 152 | 2010-2023 | |
| 26 | Bill Siple | 152 | 2002-2012 | |
| 29 | Nicolas Vargas | 151 | 2014-2028 | |
| 30 | Charles Midgett | 146 | 2002-2013 | |
| 30 | Ed Scull | 146 | 2003-2018 | |
| 32 | Qing-hua Tso# | 142 | 2019-2035 | |
| 33 | Tian-bai Chen# | 141 | 2024-2035 | |
| 34 | Brad Buckley | 139 | 2011-2028 | |
| 34 | Thomas Cohen | 139 | 2010-2019 | |
| 34 | Kevin Lambert | 139 | 2018-2031 | |
| 37 | Wendell Sorg | 138 | 2002-2011 | |
| 38 | Dave Klein# | 137 | 2022-2035 | |
| 38 | Joong-geun Yi# | 137 | 2026-2035 | |
| 40 | Ronald Adorno | 136 | 2009-2021 | |
| 41 | Víctor Rivera# | 135 | 2025-2035 | |
| 41 | Richard Shipp | 135 | 2009-2022 | |
| 43 | Joe Daye | 132 | 2002-2012 | |
| 44 | Sherman Wheeler | 131 | 2004-2015 | |
| 45 | Emílio Romero | 130 | 2019-2029 | |
| 46 | Luis Salazar# | 128 | 2023-2035 | |
| 47 | Luis Diaz | 127 | 2002-2010 | |
| 48 | Jeffrey Brunton | 125 | 2011-2024 | |
| 48 | Hector Orozco | 125 | 2007-2020 | |
| 50 | John Cooper | 122 | 2017-2030 | |
| 51 | Juan Ramírez# | 120 | 2025-2035 | |
| 51 | Joshua Stoker | 120 | 2013-2032 | |
| 53 | Gregg Fiala | 119 | 2014-2033 | |
| 53 | Timothy Vallejo* | 119 | 2005-2023 | |
| 55 | Allen Rueter | 118 | 2011-2022 | |
| 55 | Earle Stollings | 118 | 2002-2011 | |
| 57 | William Brooks# | 116 | 2028-2035 | |
| 57 | Sabas Delvalle | 116 | 2007-2016 | |
| 57 | Pio Ramirez | 116 | 2013-2024 | |
| 57 | Arturo Zavala | 116 | 2018-2033 | |
| 61 | Jermaine Earp | 115 | 2015-2028 | |
| 62 | Danny Andrews | 113 | 2011-2024 | |
| 63 | John Ryan# | 112 | 2027-2035 | |
| 63 | Eric Setliff | 112 | 2002-2011 | |
| 65 | Thomas Brasfield | 111 | 2011-2024 | |
| 65 | Bill Tussey | 111 | 2008-2019 | |
| 67 | Santos Gonzalez | 110 | 2005-2020 | |
| 67 | Roy Vaz | 110 | 2006-2018 | |
| 69 | Greg Jenkins# | 109 | 2025-2035 | |
| 70 | Jim Walton | 108 | 2021-2034 | |
| 71 | Jesus Morales | 107 | 2011-2021 | |
| 71 | Kieran Rose# | 107 | 2027-2035 | |
| 73 | Jack Kaiser# | 106 | 2023-2035 | |
| 74 | Russ Singleton# | 105 | 2026-2035 | |
| 75 | José Montáñez# | 104 | 2025-2035 | |
| 75 | Casey Plunk | 104 | 2002-2011 | |
| 77 | Ramon Garcia | 102 | 2022-2030 | |
| 77 | Steven Jurgens | 102 | 2002-2008 | |
| 77 | Troy Nelson | 102 | 2002-2010 | |
| 80 | Brendan Divine# | 101 | 2028-2035 | |
| 80 | John Kautz | 101 | 2017-2027 | |
| 82 | Rico Padua | 100 | 2014-2027 | |
| 83 | Anibal Ottman | 99 | 2014-2022 | |
| 83 | Jonathan Starner | 99 | 2002-2011 | |
| 85 | Kenneth Byers | 98 | 2010-2021 | |
| 85 | Scott Loman | 98 | 2015-2028 | |
| 85 | Roberto Olivas | 98 | 2002-2011 | |
| 88 | Juan Guerrera | 97 | 2015-2032 | |
| 89 | Ferdinand Pineda | 95 | 2013-2020 | |
| 90 | Albert Boll | 93 | 2002-2013 | |
| 90 | Jesús García | 93 | 2022-2031 | |
| 92 | Peter Bird | 92 | 2002-2012 | |
| 92 | Bradford Mcgreevy | 92 | 2007-2015 | |
| 94 | Michael Friday | 91 | 2014-2025 | |
| 94 | Gene Icenhour | 91 | 2002-2011 | |
| 96 | Carlos Rivera# | 90 | 2027-2035 | |
| 97 | Alejandro Báez# | 89 | 2028-2035 | |
| 97 | Junior Cuomo* | 89 | 2004-2023 | |
| 97 | Jose Delagarza | 89 | 2003-2012 | |
| 97 | Iván Gallardo | 89 | 2021-2032 |
