| Season | Pitcher | Team | Wins |
|---|---|---|---|
| 1885-86 | Adolfo Lujan | Habana | 5-0 |
| 1886-87 | Adolfo Lujan | Habana | 5-0 |
| 1887-88 | Francisco Hernandez | Fe | 10-2 |
| 1888-89 | Adolfo Lujan | Habana | 10-3 |
| 1889-90 | Miguel Prats | Habana | 11-2 |
| 1890-91 | Miguel Prats | Habana | 9-4 |
| 1891-92 | Emilio Hernandez | Fe | 4-1 |
| 1892-93 | Francisco Hernandez | Habana | 4-1 |
| 1893-94 | Jose Pastoriza | Almendares | 16-7 |
| 1894-95 | Enrique Garcia | Habana | 12-4 |
| 1898-99 | Jose Romero | Habanista | 5-2 |
| 1900 | Luis Padron | Habana | 13-4 |
| 1901 | Carlos Royer | Habana | 12-3 |
| 1902 | Carlos Royer | Habana | 17-0 |
| 1903 | Candido Fontales | Fe | 16-9 |
| 1904 | Carlos Royer | Habana | 13-3 |
| 1905 | Angel D'Meza | Almendares | 10-4 |
| 1906 | Jose Muñoz | Almendares | 8-1 |
| 1907 | George Mack | Habana | 4-2 |
| 1908 | Jose Mendez | Almendares | 9-0 |
| 1908-09 | Jose Mendez | Almendares | 15-6 |
| Louis Haggerman | Habana | 15-6 | |
| 1910 | Jose Mendez | Almendares | 7-0 |
| 1910-11 | Jose Mendez | Almendares | 11-2 |
| 1912 | Jose Junco | Habana | 6-1 |
| 1913 | Red Redding | Fe | 7-2 |
| 1913-14 | Jose Mendez | Almendares | 10-0 |
| 1914-15 | Jose Acosta | Habana | 5-1 |
| 1915-16 | Jose Acosta | Habana | 8-3 |
| 1917 | Jose Acosta | Orientales | 2-1 |
| 1918-19 | Jose Acosta | Habana | 16-10 |
| 1919-20 | Emilio Palmero | Almendares | 5-1 |
| 1920-21 | Jose Hernandez | Almendares | 4-1 |
| 1921 | Julio LeBlanc | Habana | 2-0 |
| 1922-23 | Lucas Boada | Marianao | 10-4 |
| 1923-24 | Bill Holland | Santa Clara | 10-2 |
| 1924-25 | Jose Acosta | Almendares | 4-1 |
| 1925-26 | Cesar Alvarez | Almendares | 10-2 |
| 1926-27 | Juan Olmo | Habana | 3-0 |
| 1927-28 | Oscar Levis | Habana | 7-2 |
| 1928-29 | Adolfo Luque | Cuba, Habana | 9-2 |
| 1929-30 | T. Yoyo Diaz | Cienfuegos | 13-3 |
| 1931-32 | Juan Eckelson | Almendares | 5-1 |
| 1932-33 | Jesus Lorenzo | Almendares | 3-0 |
| 1934-35 | Lazaro Salazar | Marianao, Almedares | 6-1 |
| 1935-36 | Martin Dihigo | Santa Clara | 11-2 |
| 1936-37 | Raymond Brown | Santa Clara | 21-4 |
| 1937-38 | Raymond Brown | Santa Clara | 12-5 |
| 1938-39 | Martin Dihigo | Habana | 14-2 |
| 1939-40 | Rodolfo Fernandez | Almendares | 7-4 |
| 1940-41 | Gilberto Torres | Habana | 10-3 |
| 1941-42 | Agapito Mayor | Almendares | 6-2 |
| Max Macon | Cienfuegos | 6-2 | |
| 1942-43 | Manuel Garcia | Habana | 10-3 |
| 1943-44 | Martin Dihigo | Habana | 8-1 |
| 1944-45 | Oliverio Ortiz | Almendares | 10-4 |
| 1945-46 | Adrian Zabala | Cienfuegos | 9-3 |
| 1946-47 | Manuel Garcia | Habana | 10-3 |
| 1947-48 | Conrado Marrero | Almendares | 12-2 |
| 1948-49 | Octavio Rubert | Almendares | 8-1 |
| 1949-50 | Octavio Rubert | Almendares | 5-1 |
| 1950-51 | Vicente Lopez | Almendares | 7-3 |
| 1951-52 | Joe Black | Cienfuegos | 15-6 |
| 1952-53 | Robert Alexander | Habana | 10-3 |
| 1953-54 | Cliff Fanning | Almendares | 13-4 |
| 1954-55 | Joe Hatten | Almendares | 13-5 |
| 1955-56 | Pedro Ramos | Cienfuegos | 13-5 |
| 1956-57 | Camilo Pascual | Cienfuegos | 15-5 |
| 1957-58 | Billy O'Dell | Almendares | 7-2 |
| 1958-59 | Orlando Peña | Almendares | 13-5 |
| 1959-60 | Camilo Pascual | Cienfuegos | 15-5 (.750) |
| Raul Sanchez | Cienfuegos | 12-4 (.750) | |
| 1960-61 | Pedro Ramos | Cienfuegos | 16-7 |
Champion pitchers
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