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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Josh Jones | 221 | 1901-1914 | |
| 2 | Norberto Hernández | 215 | 1903-1914 | |
| 3 | Ewan Baxter | 209 | 1901-1914 | |
| 4 | Aidan Grant | 208 | 1901-1914 | |
| 5 | Louis Cohen | 203 | 1901-1913 | |
| 6 | Kian Sells | 190 | 1901-1913 | |
| 7 | Billy Evans | 181 | 1901-1912 | |
| 8 | Hernán Ocampo# | 180 | 1903-1913 | |
| 9 | Ángel de Hoyos# | 172 | 1902-1910 | |
| 10 | Ángel Moreno# | 164 | 1902-1911 | |
| 11 | Dominic Hague | 162 | 1901-1913 | |
| 12 | Aldo Rodríguez# | 158 | 1903-1914 | |
| 13 | Connor Pike | 156 | 1901-1911 | |
| 14 | Ordoño Ortega | 153 | 1904-1912 | |
| 14 | Zacarías Sosa | 153 | 1904-1913 | |
| 16 | Rodulfo Camarena# | 152 | 1906-1913 | |
| 17 | Kyle Williams | 150 | 1901-1914 | |
| 18 | Luis Melchor# | 149 | 1906-1914 | |
| 19 | Federico Celaya# | 145 | 1906-1912 | |
| 20 | Rob Murphy | 144 | 1901-1911 | |
| 21 | Zak Gardner | 143 | 1901-1910 | |
| 21 | Matías Rivera# | 143 | 1903-1914 | |
| 23 | Patrick Grimley | 138 | 1901-1909 | |
| 24 | Martín León | 137 | 1902-1910 | |
| 25 | Trevor Leith | 136 | 1901-1910 | |
| 25 | Julio Morales# | 136 | 1907-1913 | |
| 27 | Antonio Triana# | 132 | 1903-1910 | |
| 28 | Ricardo Márquez | 128 | 1906-1913 | |
| 29 | José López# | 124 | 1907-1914 | |
| 29 | Báquides Sánchez# | 124 | 1902-1909 | |
| 31 | Ramón Piña | 123 | 1902-1909 | |
| 32 | Sloan Mahoney# | 122 | 1908-1914 | |
| 33 | Ramón Contreras# | 121 | 1906-1912 | |
| 33 | Ciro Robledo | 121 | 1902-1910 | |
| 35 | Jorge Flores# | 120 | 1906-1914 | |
| 35 | Avelino Oliva# | 120 | 1902-1910 | |
| 37 | Emanuel Gutiérrez | 116 | 1902-1910 | |
| 38 | Matthew McKenzie | 114 | 1901-1909 | |
| 39 | Billy Clarke | 113 | 1901-1910 | |
| 40 | Astolfo Sánchez | 112 | 1905-1913 | |
| 41 | Balduino Anaya | 111 | 1905-1911 | |
| 41 | Gideon Atkinson | 111 | 1901-1909 | |
| 41 | Randy Foley | 111 | 1901-1908 | |
| 41 | Clyde McDermott | 111 | 1901-1910 | |
| 45 | Shawn Jordan | 108 | 1901-1909 | |
| 45 | Lorenzo Maldonado# | 108 | 1906-1913 | |
| 47 | Neftalí Cabrera# | 106 | 1905-1914 | |
| 47 | Augusto Hernández# | 106 | 1906-1914 | |
| 47 | Todd Shaw | 106 | 1901-1908 | |
| 50 | Cecilio Roldán | 105 | 1904-1910 | |
| 51 | Thomas O'Reilly | 104 | 1901-1908 | |
| 51 | Jacobo Álvarez | 104 | 1906-1914 | |
| 53 | Joel Price | 103 | 1901-1911 | |
| 54 | Max Drummond | 100 | 1906-1913 | |
| 55 | Filóstrato Hernández | 99 | 1904-1913 | |
| 56 | Lester Gill | 98 | 1901-1910 | |
| 57 | Abenámar Martínez | 97 | 1903-1914 | |
| 57 | Ross Smith | 97 | 1901-1909 | |
| 59 | Angus McGrath | 96 | 1901-1913 | |
| 59 | Esteban Quezada# | 96 | 1906-1913 | |
| 61 | Aidan Clark | 95 | 1904-1910 | |
| 62 | Mateo de la Cruz# | 94 | 1906-1913 | |
| 62 | Gonzalo Presas | 94 | 1902-1910 | |
| 64 | Danilo Portillo# | 93 | 1903-1910 | |
| 65 | Vladik Ofitserov | 92 | 1906-1911 | |
| 66 | Álvaro López# | 91 | 1905-1912 | |
| 66 | Gabriel Rodríguez# | 91 | 1906-1913 | |
| 68 | Bryan Mrazek | 90 | 1901-1910 | |
| 69 | Ramiro Rendón# | 89 | 1906-1913 | |
| 70 | Louie Rogers | 88 | 1901-1909 | |
| 71 | Normando Fraire# | 87 | 1902-1906 | |
| 72 | Eher Byrne | 85 | 1901-1906 | |
| 72 | Diomedes Galván | 85 | 1906-1913 | |
| 72 | Harry Irvine | 85 | 1901-1909 | |
| 72 | Alfredo Torres# | 85 | 1907-1914 | |
| 76 | Sean Forrest | 84 | 1901-1908 | |
| 76 | Douggie Taylor | 84 | 1901-1909 | |
| 78 | Luis de Paula | 82 | 1905-1912 | |
| 78 | Cassidy Galloway | 82 | 1901-1912 | |
| 78 | Timoteo Ortega# | 82 | 1907-1913 | |
| 78 | Tony Stewart | 82 | 1901-1906 | |
| 78 | Shaun Todd | 82 | 1901-1906 | |
| 78 | Osheen Tully | 82 | 1901-1913 | |
| 84 | Bart Jones | 81 | 1901-1910 | |
| 85 | Jack Cunningham | 80 | 1901-1905 | |
| 85 | Adalberto González | 80 | 1905-1912 | |
| 85 | Charles Houston | 80 | 1901-1909 | |
| 85 | Orestes Méndez# | 80 | 1908-1914 | |
| 89 | Abdías Rodríguez | 79 | 1905-1912 | |
| 90 | Constancio Hernández# | 78 | 1909-1914 | |
| 90 | Jim Normand | 78 | 1901-1906 | |
| 92 | Danny Reid | 77 | 1901-1909 | |
| 92 | Simon Rodwell | 77 | 1901-1912 | |
| 94 | Neil Hughes | 76 | 1901-1907 | |
| 94 | Rubén Martín# | 76 | 1906-1914 | |
| 94 | Ernesto Pedraza | 76 | 1910-1914 | |
| 97 | Ernest Johnson | 75 | 1901-1906 | |
| 97 | Inocencio Rico# | 75 | 1906-1914 | |
| 99 | Joseph Galloway | 73 | 1901-1908 | |
| 99 | Justin Hudson | 73 | 1901-1907 |
