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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jorge Castillo# | 253 | 2026-2042 | |
| 1 | Markus Hancock* | 253 | 2008-2026 | |
| 3 | Francisco Robles* | 244 | 2012-2030 | |
| 4 | Kenny Ashley | 232 | 2017-2036 | |
| 5 | Manuel Corona* | 214 | 2012-2028 | |
| 6 | Yakamochi Suitani* | 212 | 2021-2034 | |
| 7 | Dean O'Monahan* | 210 | 2007-2022 | |
| 8 | Luppe van Dam# | 202 | 2029-2042 | |
| 8 | Enrique Vázquez* | 202 | 2024-2037 | |
| 10 | Randy Smith* | 201 | 2016-2032 | |
| 11 | Jim MacCowan | 193 | 2023-2038 | |
| 12 | Juan Acosta# | 184 | 2029-2042 | |
| 12 | Tony Cuellar | 184 | 2019-2035 | |
| 12 | Carlos Rivera | 184 | 2014-2031 | |
| 15 | Fred Benjamin* | 183 | 2014-2029 | |
| 15 | Clayton Lewis | 183 | 2016-2032 | |
| 17 | Michel Provost* | 178 | 2016-2030 | |
| 18 | Armando Gallegos | 176 | 2009-2024 | |
| 19 | Nelson Anderson | 175 | 2007-2017 | |
| 20 | Toby Ayers# | 174 | 2027-2042 | |
| 20 | Cristo Santiago | 174 | 2014-2033 | |
| 22 | José Cruz | 171 | 2007-2018 | |
| 22 | Roberto Rodríguez | 171 | 2010-2027 | |
| 24 | Luigi Bright | 169 | 2020-2035 | |
| 24 | Conan McCullough* | 169 | 2007-2018 | |
| 24 | Ernesto Molina | 169 | 2021-2035 | |
| 27 | Neil Maes | 167 | 2019-2032 | |
| 28 | Owen Barse# | 166 | 2030-2042 | |
| 28 | Takanobu Shirai | 166 | 2021-2036 | |
| 30 | Joe Arnold# | 164 | 2030-2042 | |
| 30 | Anastasio López | 164 | 2014-2028 | |
| 32 | Chris York* | 162 | 2012-2028 | |
| 33 | Daniel Hernández# | 159 | 2032-2042 | |
| 34 | Miguel Cantú | 158 | 2015-2028 | |
| 35 | Richard Neely | 157 | 2026-2040 | |
| 36 | Gunner MacGruder* | 156 | 2014-2029 | |
| 36 | Artie Tillman | 156 | 2007-2020 | |
| 36 | Orlando Trujillo# | 156 | 2028-2042 | |
| 39 | Dean McNeil | 153 | 2023-2038 | |
| 40 | Juan López# | 152 | 2027-2042 | |
| 40 | António Rivera | 152 | 2007-2018 | |
| 42 | Félix Maese | 151 | 2014-2027 | |
| 43 | Jeffrey Mendoza# | 148 | 2028-2042 | |
| 44 | Hiroyuki Nii | 147 | 2014-2024 | |
| 45 | Bill Lewis | 143 | 2012-2027 | |
| 45 | Javier Sáenz | 143 | 2011-2027 | |
| 47 | Mathys Crête | 140 | 2007-2018 | |
| 47 | Duane Moss# | 140 | 2031-2042 | |
| 49 | Cedric Mosley | 139 | 2007-2018 | |
| 50 | George Lee | 138 | 2018-2031 | |
| 51 | Kijuro Kojima | 137 | 2007-2015 | |
| 51 | John Turner | 137 | 2021-2037 | |
| 51 | Alfredo Velázquez | 137 | 2014-2026 | |
| 54 | Carlos Pérez | 136 | 2020-2035 | |
| 55 | Conner Hurst | 135 | 2017-2033 | |
| 55 | Edgardo Trevino# | 135 | 2033-2042 | |
| 57 | Chris Brown# | 134 | 2027-2040 | |
| 57 | Luis Gusmán | 134 | 2016-2028 | |
| 59 | Tsuramatsu Ito | 133 | 2018-2033 | |
| 59 | Hen-to Tse# | 133 | 2035-2042 | |
| 59 | Pat Willis# | 133 | 2028-2038 | |
| 62 | Ángel Valdéz | 132 | 2027-2037 | |
| 63 | Brenden Clymo# | 131 | 2033-2042 | |
| 63 | Carmelo Lamberti# | 131 | 2033-2042 | |
| 65 | Iwane Sato | 130 | 2021-2032 | |
| 66 | Sa-yoor Ch'oe# | 129 | 2032-2042 | |
| 66 | John Ross# | 129 | 2031-2042 | |
| 68 | José Hernández | 128 | 2020-2033 | |
| 68 | Erik Watson | 128 | 2026-2038 | |
| 70 | Kata Nakamura | 127 | 2020-2031 | |
| 71 | Félix Ortega | 126 | 2011-2020 | |
| 72 | Henry Cluett# | 125 | 2030-2041 | |
| 72 | Bartolo Esquivel | 125 | 2021-2032 | |
| 72 | Jorge Medina | 125 | 2027-2038 | |
| 75 | Cheong-sang Yun# | 123 | 2031-2042 | |
| 76 | Todd Burns | 122 | 2013-2025 | |
| 76 | Carlos Fernández | 122 | 2017-2028 | |
| 76 | Víctor Matos | 122 | 2007-2016 | |
| 76 | Dylan Mcintosh | 122 | 2027-2037 | |
| 80 | José Fernández | 121 | 2027-2036 | |
| 81 | Eric Elliott | 120 | 2025-2038 | |
| 81 | Martín Francisco | 120 | 2013-2024 | |
| 81 | Kensaku Gato | 120 | 2021-2037 | |
| 81 | Roberto Rivera# | 120 | 2032-2042 | |
| 85 | Manuel Gonzáles# | 119 | 2029-2042 | |
| 85 | Randy Zimmerman# | 119 | 2026-2039 | |
| 87 | Chandler Davis | 118 | 2007-2016 | |
| 87 | Jonathan Sherwin | 118 | 2024-2036 | |
| 87 | Dong-hak Yi# | 118 | 2034-2042 | |
| 90 | Michael Doyle# | 117 | 2032-2042 | |
| 90 | Alfredo Gonzáles# | 117 | 2032-2042 | |
| 90 | Iwao Maruyama | 117 | 2027-2038 | |
| 90 | Julián Thomas | 117 | 2017-2028 | |
| 94 | Bang-xao Niu# | 116 | 2031-2042 | |
| 95 | Armando Batista# | 115 | 2032-2042 | |
| 95 | Juan Cervantes | 115 | 2021-2034 | |
| 95 | Alberto Flores# | 115 | 2033-2042 | |
| 95 | Gustavo Hernández# | 115 | 2029-2042 | |
| 95 | Tatsui Kouno | 115 | 2018-2028 | |
| 95 | Bryan Stewart | 115 | 2007-2015 |
