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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jeffrey Lebowski* | 351 | 2017-2037 | |
| 2 | Stephen Dundee# | 340 | 2060-2076 | |
| 3 | Tomás González* | 329 | 2048-2069 | |
| 4 | Don Edwards* | 328 | 2049-2068 | |
| 5 | Chad Frederick* | 327 | 1998-2016 | |
| 6 | Ángel Sierra* | 321 | 2031-2051 | |
| 7 | Arturo Marquez* | 317 | 1999-2019 | |
| 7 | Robert Nagle* | 317 | 2025-2042 | |
| 9 | Rick Ball* | 306 | 2051-2070 | |
| 10 | Edgar Dailey* | 305 | 2043-2057 | |
| 10 | Spencer Mitchell* | 305 | 2014-2029 | |
| 10 | Micah Ward* | 305 | 2029-2048 | |
| 13 | Nate Ward* | 301 | 2046-2062 | |
| 14 | Paul Williams | 291 | 2051-2071 | |
| 15 | Harold Freeman* | 287 | 2014-2029 | |
| 16 | Jeffrey Lyle* | 276 | 2015-2033 | |
| 17 | Timothy Chaparro | 275 | 2008-2023 | |
| 17 | Steve Morrow* | 275 | 2040-2059 | |
| 19 | Ollie Gilbert* | 266 | 2032-2050 | |
| 19 | David Warren* | 266 | 2020-2035 | |
| 21 | Javier García | 263 | 2052-2074 | |
| 22 | Amando Hernandez* | 262 | 2014-2030 | |
| 23 | José Alba | 261 | 2052-2072 | |
| 23 | Steve Cook* | 261 | 2047-2066 | |
| 23 | Joseph Woodard | 261 | 2005-2022 | |
| 26 | Juan Tirado* | 260 | 2030-2046 | |
| 26 | Chris Topper* | 260 | 2015-2030 | |
| 28 | Paul Woods | 255 | 2004-2019 | |
| 29 | Scott Primmer* | 253 | 2011-2028 | |
| 30 | Frank Agarwal | 249 | 2002-2019 | |
| 30 | Chang Kaufmann | 249 | 2007-2021 | |
| 30 | Randy Sloss* | 249 | 2014-2029 | |
| 33 | Gaby Rodriguez* | 243 | 1999-2016 | |
| 34 | Luis Martínez* | 238 | 2033-2052 | |
| 35 | Ron Collins# | 237 | 2060-2076 | |
| 36 | Bryan Bormann | 236 | 2024-2042 | |
| 36 | Anthony Murray* | 236 | 2029-2048 | |
| 38 | Juan Vargas | 234 | 2056-2075 | |
| 39 | Juan Acuña* | 231 | 2015-2027 | |
| 40 | Loren Berrian* | 230 | 2021-2040 | |
| 40 | Samuel Corley* | 230 | 2042-2057 | |
| 40 | Larry Hodge | 230 | 2028-2045 | |
| 43 | George Hernández* | 229 | 2044-2059 | |
| 44 | Osvaldo Veiga | 226 | 2017-2035 | |
| 45 | Eloy Garcia | 225 | 2009-2023 | |
| 45 | William Martin | 225 | 2005-2022 | |
| 45 | Thomas Rodriques | 225 | 2021-2034 | |
| 48 | Jesus Quintana* | 223 | 2016-2029 | |
| 49 | Cruz Abad | 221 | 2000-2016 | |
| 49 | Bill Chapa | 221 | 2003-2019 | |
| 49 | William Echeverria* | 221 | 2015-2029 | |
| 52 | Juan Santana* | 219 | 2038-2054 | |
| 53 | Jesus Ferreira* | 218 | 2000-2017 | |
| 54 | Samuel Pettie | 217 | 2003-2020 | |
| 55 | Eugene Sampson | 213 | 2028-2046 | |
| 55 | Mario Segura* | 213 | 2051-2066 | |
| 55 | Bob Young | 213 | 2017-2033 | |
| 58 | Tony Canales | 212 | 2039-2055 | |
| 58 | Wilfredo Rivero | 212 | 2002-2019 | |
| 60 | Herman Corcoran* | 211 | 2014-2029 | |
| 61 | Jacob Harris | 210 | 2038-2053 | |
| 61 | David Phillips* | 210 | 2019-2030 | |
| 63 | Donald Parks | 209 | 2033-2052 | |
| 64 | William Jones | 208 | 2029-2043 | |
| 65 | Ramon Castro | 206 | 2014-2028 | |
| 65 | Francisco Ledesma | 206 | 2039-2055 | |
| 67 | John Meader | 205 | 1998-2014 | |
| 68 | Kenneth Benton | 204 | 2024-2038 | |
| 68 | Terry Cowles | 204 | 2012-2025 | |
| 68 | Oscar Pineda | 204 | 2034-2051 | |
| 68 | Eric Shaw* | 204 | 1998-2012 | |
| 72 | Leo Aguirre | 203 | 2000-2015 | |
| 72 | Felipe Delgado# | 203 | 2063-2076 | |
| 74 | José Nava | 202 | 2044-2062 | |
| 75 | Ricardo Banda | 201 | 2013-2029 | |
| 75 | Rodney Linker | 201 | 2001-2017 | |
| 75 | Tomás Quintero | 201 | 2058-2074 | |
| 75 | Matthew Williams | 201 | 2023-2038 | |
| 79 | Osvaldo Rivera | 200 | 2023-2037 | |
| 80 | Greg Canseco# | 198 | 2058-2076 | |
| 80 | Jesse Parker# | 198 | 2059-2076 | |
| 82 | Edward Maloof | 195 | 2017-2030 | |
| 82 | George Skinner | 195 | 2060-2074 | |
| 84 | Michael Holtman | 194 | 2009-2028 | |
| 84 | William Prim | 194 | 2025-2041 | |
| 86 | Brian Gilmer | 193 | 2001-2013 | |
| 86 | Elvin Lawson# | 193 | 2057-2076 | |
| 88 | Jonathan Barner | 191 | 2021-2036 | |
| 89 | Lindsey Butterworth | 190 | 2023-2041 | |
| 90 | Ricardo Dapena | 189 | 2004-2020 | |
| 90 | Carlos Ojeda | 189 | 2029-2043 | |
| 90 | Edwin Sutton | 189 | 2042-2056 | |
| 90 | Kevin Underwood# | 189 | 2062-2076 | |
| 94 | Joel Lopez | 188 | 2011-2025 | |
| 95 | Ricardo Colón | 187 | 2050-2066 | |
| 95 | Joseph Gray | 187 | 2018-2033 | |
| 95 | Luis Santiago Jr.# | 187 | 2061-2076 | |
| 95 | David Thornton | 187 | 2045-2064 | |
| 99 | Michael Rushton | 186 | 2023-2038 | |
| 100 | Hoyt Murphy# | 185 | 2058-2076 |
