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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Bill Phyle# | 222 | 1904-1915 | |
| 2 | Jack Stivetts | 208 | 1904-1914 | |
| 3 | Andres Ortega# | 197 | 1904-1915 | |
| 4 | Nicolás Casas# | 193 | 1904-1915 | |
| 5 | Darío Domínguez# | 187 | 1906-1915 | |
| 6 | Amadeo Jiménez# | 184 | 1904-1915 | |
| 7 | Peichun Tan# | 179 | 1905-1915 | |
| 8 | Pedro Olave# | 174 | 1904-1915 | |
| 9 | Ross Best# | 170 | 1904-1915 | |
| 10 | Damian Freake | 169 | 1905-1915 | |
| 11 | Bill Donovan# | 164 | 1904-1913 | |
| 12 | Red Ames# | 163 | 1904-1915 | |
| 12 | Josh Cornaby# | 163 | 1904-1915 | |
| 14 | Agustín Acosta# | 161 | 1904-1915 | |
| 15 | Alejandro Urbina# | 160 | 1906-1915 | |
| 16 | Ricardo Cruz# | 159 | 1906-1915 | |
| 17 | F. Scott# | 157 | 1904-1915 | |
| 18 | Pol Brennan# | 156 | 1906-1914 | |
| 19 | Beany Jacobson# | 154 | 1904-1915 | |
| 20 | Nepomuceno Muñoz# | 153 | 1906-1915 | |
| 20 | Eusebio Ortiz# | 153 | 1906-1913 | |
| 22 | Marcos Gerena# | 151 | 1906-1915 | |
| 22 | Mateo Regalado# | 151 | 1906-1915 | |
| 24 | Constancio Medina# | 148 | 1904-1915 | |
| 25 | Gerardo Domínguez | 147 | 1904-1913 | |
| 25 | Matt Patterson | 147 | 1905-1914 | |
| 25 | Rip Ragan# | 147 | 1904-1915 | |
| 28 | Jake Ricci# | 144 | 1905-1915 | |
| 29 | Hiram Sierra# | 143 | 1904-1915 | |
| 30 | Pablo Cortés# | 142 | 1904-1915 | |
| 30 | Ramón Durán# | 142 | 1906-1915 | |
| 32 | Atanasio Balbuena# | 141 | 1906-1915 | |
| 32 | Javier García# | 141 | 1906-1915 | |
| 32 | Joe O'Toole | 141 | 1905-1915 | |
| 35 | Leonardo Bonilla# | 137 | 1906-1915 | |
| 35 | Mateo Ramírez# | 137 | 1906-1915 | |
| 37 | Sabino Flores# | 135 | 1904-1915 | |
| 37 | Luis García# | 135 | 1906-1915 | |
| 39 | Anaxímenes Valverde# | 134 | 1907-1915 | |
| 40 | Seth Braden | 133 | 1905-1914 | |
| 40 | Eduardo García | 133 | 1904-1913 | |
| 42 | Ciriaco Méndez# | 131 | 1907-1915 | |
| 43 | Joël Coutant# | 130 | 1906-1915 | |
| 44 | Carl Leah | 128 | 1905-1912 | |
| 44 | Antonio Sánchez# | 128 | 1905-1915 | |
| 46 | Brandon Brown | 127 | 1904-1912 | |
| 47 | Toribio Gamboa# | 126 | 1906-1915 | |
| 47 | Alejandro Rivera# | 126 | 1906-1915 | |
| 47 | Tony Schmidt | 126 | 1905-1914 | |
| 50 | Manuel Martines# | 125 | 1906-1913 | |
| 51 | José Arce# | 124 | 1904-1915 | |
| 51 | Silvio Ramírez | 124 | 1905-1915 | |
| 53 | Yohann Bessé | 123 | 1905-1913 | |
| 54 | Julián Rey# | 122 | 1906-1915 | |
| 55 | Omar Martínez# | 120 | 1906-1915 | |
| 56 | Carlos Sosa# | 119 | 1907-1915 | |
| 57 | Enrique Ocampo# | 118 | 1906-1912 | |
| 58 | Rich Tucker | 117 | 1905-1914 | |
| 59 | Uranio Avitia# | 116 | 1907-1915 | |
| 59 | Darío Mendoza# | 116 | 1905-1915 | |
| 59 | Jack Pfiester | 116 | 1904-1915 | |
| 62 | Phil Ladner | 115 | 1905-1914 | |
| 63 | Fausto Guerrero# | 114 | 1906-1915 | |
| 64 | Stewart Hunter | 113 | 1905-1915 | |
| 65 | Bernard Hawkins | 112 | 1906-1914 | |
| 65 | Josh Kelso# | 112 | 1905-1915 | |
| 65 | Brock Whitford# | 112 | 1905-1915 | |
| 68 | George Davies | 111 | 1904-1914 | |
| 68 | Michael Holwell | 111 | 1904-1915 | |
| 68 | Venancio Rivera# | 111 | 1904-1915 | |
| 68 | Jesse Wilson# | 111 | 1905-1915 | |
| 72 | Telesforo Mata# | 108 | 1904-1915 | |
| 73 | Martín Torres# | 106 | 1906-1915 | |
| 74 | Gabriel Pérez | 105 | 1904-1914 | |
| 75 | Mateo Martínez# | 104 | 1907-1915 | |
| 76 | Ron Barker# | 103 | 1905-1915 | |
| 76 | Francisco López# | 103 | 1908-1915 | |
| 78 | Ian Cooper | 102 | 1904-1914 | |
| 79 | Aldomiro González# | 101 | 1904-1911 | |
| 79 | Mamerto Hernández | 101 | 1904-1914 | |
| 79 | Luis Zacarías# | 101 | 1906-1915 | |
| 82 | Nerón Solano# | 100 | 1904-1915 | |
| 83 | Rich Crowley | 99 | 1905-1914 | |
| 83 | Gilberto Moreira# | 99 | 1906-1915 | |
| 85 | Vicente Herrera# | 98 | 1906-1915 | |
| 86 | Cole Gagnon | 97 | 1905-1915 | |
| 87 | Marcelino Jaques# | 96 | 1904-1915 | |
| 88 | Aluino de Varona | 95 | 1904-1911 | |
| 89 | Coleman Reeves | 93 | 1905-1914 | |
| 90 | John Callahan# | 92 | 1905-1915 | |
| 90 | Jake Glover | 92 | 1905-1915 | |
| 92 | Modesto Chávez# | 91 | 1908-1913 | |
| 92 | Jose Fernandez# | 91 | 1906-1915 | |
| 94 | Valerio Álvarez# | 90 | 1906-1915 | |
| 95 | Vaughan Mullins | 89 | 1907-1914 | |
| 96 | Agapito de la Rosa# | 88 | 1904-1915 | |
| 96 | Gus Dorner | 88 | 1904-1913 | |
| 96 | Earl Eby | 88 | 1905-1914 | |
| 99 | Bob Cashmann | 86 | 1905-1915 | |
| 99 | Norm Smith | 86 | 1905-1914 |
