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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Esteban Ramírez* | 309 | 2028-2046 | |
| 2 | Brian Hicks# | 297 | 2034-2051 | |
| 2 | Wilson Sostenes# | 297 | 2031-2051 | |
| 4 | Millard Johnston* | 282 | 2016-2036 | |
| 5 | Kenny Beasley* | 277 | 2027-2046 | |
| 6 | Dan Davenport* | 258 | 2029-2048 | |
| 7 | Lynn Lawrence* | 255 | 2020-2041 | |
| 8 | B.J. Young# | 239 | 2037-2051 | |
| 9 | Lou Godfrey* | 238 | 2030-2045 | |
| 10 | Brit Clark* | 232 | 2029-2046 | |
| 11 | Russ Humby* | 227 | 2019-2035 | |
| 12 | Ken Russell* | 226 | 2023-2040 | |
| 13 | Christian Cooper* | 222 | 2021-2036 | |
| 14 | Todd Brown# | 221 | 2038-2051 | |
| 14 | Daniel Myers | 221 | 2027-2046 | |
| 16 | Dan Harper* | 220 | 2018-2035 | |
| 17 | Juan Varela* | 216 | 2024-2039 | |
| 18 | Matt Hughes* | 213 | 2029-2046 | |
| 19 | Miguel Hernández* | 212 | 2024-2039 | |
| 20 | Herbert Christianson | 211 | 2011-2028 | |
| 21 | Will Lester | 206 | 2023-2041 | |
| 22 | Jorge Ramírez* | 205 | 2020-2036 | |
| 23 | Joseph Burns | 204 | 2035-2051 | |
| 24 | Vincent Harrison | 202 | 2031-2047 | |
| 25 | Steven Ramon* | 201 | 2011-2024 | |
| 26 | Joey Aragon* | 200 | 2010-2025 | |
| 27 | José López | 192 | 2030-2046 | |
| 27 | Fernando Ortíz | 192 | 2029-2044 | |
| 27 | Sergio Torres* | 192 | 2015-2029 | |
| 30 | Pancho Lugo# | 189 | 2038-2051 | |
| 31 | Adrian Lee* | 188 | 2012-2025 | |
| 32 | Bartolo Hernández | 186 | 2029-2044 | |
| 33 | Brad Heller | 185 | 2024-2039 | |
| 33 | Emílio Romero | 185 | 2030-2048 | |
| 35 | Everett Barber | 184 | 2021-2035 | |
| 35 | Preston Pace | 184 | 2013-2028 | |
| 37 | John Crumb* | 183 | 2010-2025 | |
| 37 | Anthony Peterson | 183 | 2013-2030 | |
| 39 | Reginald Dyer* | 182 | 2016-2029 | |
| 40 | Cal Hall | 181 | 2021-2039 | |
| 40 | Carl Hart* | 181 | 2028-2044 | |
| 42 | Sergio Torres | 180 | 2028-2047 | |
| 43 | Bill Dennis | 179 | 2031-2046 | |
| 43 | António Patino | 179 | 2019-2033 | |
| 45 | José Saucedo | 178 | 2012-2026 | |
| 46 | Bob Powell | 176 | 2027-2040 | |
| 47 | Terrence Carter | 175 | 2011-2024 | |
| 48 | Daniel González | 174 | 2013-2026 | |
| 48 | Artie Harris | 174 | 2017-2033 | |
| 48 | Bryan Pickett* | 174 | 2019-2033 | |
| 51 | Randy Ryan | 173 | 2030-2044 | |
| 52 | Gunner Bailey | 172 | 2015-2029 | |
| 52 | Javier Martínez | 172 | 2035-2050 | |
| 54 | James Varnell | 171 | 2009-2022 | |
| 54 | Floyd Weston# | 171 | 2036-2051 | |
| 56 | Ramón Padilla | 168 | 2035-2048 | |
| 57 | Chris Gregory | 167 | 2020-2037 | |
| 57 | Donald Wiggins | 167 | 2035-2050 | |
| 59 | William Stone* | 166 | 2012-2022 | |
| 60 | José Romano | 165 | 2026-2040 | |
| 61 | Tyler Beeman | 164 | 2029-2042 | |
| 61 | Jeff Moore | 164 | 2032-2045 | |
| 63 | Todd Burton# | 163 | 2039-2051 | |
| 63 | Fredrick Planas | 163 | 2008-2020 | |
| 63 | Tim Whaley# | 163 | 2038-2051 | |
| 66 | Gerald Fox | 162 | 2016-2030 | |
| 66 | Mike Gabbard# | 162 | 2037-2051 | |
| 68 | Ian Robeson | 161 | 2018-2033 | |
| 69 | Robinson Hill* | 160 | 2022-2032 | |
| 70 | César Gómez | 159 | 2012-2028 | |
| 71 | Bill Black* | 158 | 2029-2042 | |
| 72 | C.J. Tyler | 157 | 2010-2024 | |
| 73 | Juan Flores | 156 | 2024-2034 | |
| 73 | Domingo Trevino | 156 | 2036-2051 | |
| 75 | William Landeros | 155 | 2011-2024 | |
| 75 | Jesús Pimentel | 155 | 2015-2031 | |
| 75 | Pat Rice | 155 | 2017-2029 | |
| 78 | Josh Lord | 152 | 2018-2030 | |
| 79 | Nate Forrest | 150 | 2016-2032 | |
| 79 | John Porter | 150 | 2008-2020 | |
| 79 | Mark Townsley# | 150 | 2042-2051 | |
| 82 | Dover Graves | 149 | 2016-2030 | |
| 82 | Bill McConnell | 149 | 2019-2031 | |
| 82 | Manuel Vega | 149 | 2026-2041 | |
| 85 | Horace Bush# | 148 | 2041-2051 | |
| 86 | Phil Briggs | 145 | 2009-2023 | |
| 87 | Telmo Badanha* | 144 | 2028-2041 | |
| 87 | Kevin Jackson | 144 | 2026-2038 | |
| 89 | Rob Hayes | 143 | 2017-2031 | |
| 89 | Randy Littlejohn | 143 | 2027-2038 | |
| 91 | Jonas Arispe | 142 | 2009-2023 | |
| 91 | Phillip McCants | 142 | 2011-2026 | |
| 91 | Rubén Sánchez# | 142 | 2038-2051 | |
| 94 | Millard Blyth | 138 | 2030-2046 | |
| 94 | Pat Hunt | 138 | 2032-2045 | |
| 96 | Larry Mosley | 136 | 2035-2047 | |
| 97 | Duane Pérez | 135 | 2035-2046 | |
| 98 | Dave Keller | 134 | 2032-2047 | |
| 98 | Arthur Richards | 134 | 2027-2041 | |
| 100 | William Morgan | 133 | 2036-2048 |
