| Season | Winning team | Manager |
|---|---|---|
| 1878-79 | Habana | Esteban Bellan |
| 1879-80 | Habana | Esteban Bellan |
| 1882-83 | habana | Esteban Bellan |
| 1885 | Habana | Ricardo Mora |
| 1885-86 | Habana | Francisco Saavedra |
| 1886-87 | Habana | Francisco Saavedra |
| 1887-88 | Fe | Antonio Utrera |
| 1888-89 | Habana | Emilio Sabourin |
| 1889-90 | Habana | Emilio Sabourin |
| 1890-91 | Fe | Luis Almoina |
| 1891-92 | Habana | Emilio Sabourin |
| 1892-93 | Matanza | Luis Almoina |
| 1893-94 | Almendares | Ramon Gutierrez |
| 1898-99 | Habanista | Alberto Azoy |
| 1900 | San Francisco | Patricio Silverio |
| 1901 | Habana | Alberto Azoy |
| 1902 | Habana | Alberto Azoy |
| 1903 | Habana | Alberto Azoy |
| 1904 | Habana | Alberto Azoy |
| 1805 | Almendares | Abel Linares |
| 1906 | Fe | Alberto Azoy |
| 1907 | Almendares | Eugenio Santa Cruz |
| 1908 | Almendares | Juan Sanchez |
| 1908-09 | Habana | Luis Someillan |
| 1910 | Almendares | Juan Sanchez |
| 1910-11 | Almendares | Juan Sanchez |
| 1912 | Habana | Eduardo Laborde |
| 1913 | Fe | Agustin (Tinti) Molina |
| 1913-14 | Almendares | Eugenio Santa Cruz |
| 1914-15 | Habana | Miguel Angel Gonzalez |
| 1915-16 | Almendares | Alfredo Cabrera |
| 1917 | Orientals | Amando Marsans |
| 1918-19 | Habana | Miguel Angel Gonzalez |
| 1919-20 | Almendares | Adolfo Luque |
| 1920-21 | Habana | Miguel Angel Gonzalez |
| 1921 | Habana | Miguel Angel Gonzalez |
| 1922-23 | Marianao | Baldomero (Mertio) Acosta |
| 1923-24 | Santa Clara | Agustin (Tinti) Molina |
| 1924-25 | Almendares | Joseito Rodriguez |
| 1925-26 | Almendares | Joseito Rodriguez |
| 1926-27 | Habana | Miguel Angel Gonzalez |
| 1926-27 (Triangular) | Alacranes | Adolfo Luque |
| 1927-28 | Habana | Miguel Angel Gonzalez |
| 1928-29 | Habana | Miguel Angel Gonzalez |
| 1929-30 | Cienfuegos | Pelayo Chacon |
| 1931-32 | Almendares | Joseito Rodriguez |
| 1932-33 | Almendares (tie) | Adolfo Luque |
| Habana (tie) | Miguel Angel Gonzalez | |
| 1934-35 | Almendares | Adolfo Luque |
| 1935-36 | Santa Clara | Martin Dihigo |
| 1936-37 | Marianao | Martin Dihigo |
| 1937-38 | Santa Clara | Lazaro Salazar |
| 1938-39 | Santa Clara | Lazaro Salazar |
| 1939-40 | Almendares | Adolfo Luque |
| 1940-41 | Habana | Miguel Angel Gonzalez |
| 1941-42 | Almendares | Adolfo Luque |
| 1942-43 | Almendares | Adolfo Luque |
| 1943-44 | Habana | Miguel Angel Gonzalez |
| 1944-45 | Almendares | Reinaldo Cordeiro |
| 1945-46 | Cienfuegos | Adolfo Luque |
| 1946-47 | Almendares | Adolfo Luque |
| 1946-47 (National) | Matanzas | Silvio Garcia |
| 1947-48 | Habana | Miguel Angel Gonzalez |
| 1947-48 (Players) | Leones | Salvador Hernandez |
| 1948-49 | Almendares | Fermin Guerra |
| 1949-50 | Almendares | Fermin Guerra |
| 1950-51 | Habana | Miguel Angel Gonzalez |
| 1951-52 | Habana | Miguel Angel Gonzalez |
| 1952-53 | Habana | Miguel Angel Gonzalez |
| 1953-54 | Almendares | Bobby Bragan |
| 1954-55 | Almendares | Bobby Bragan |
| 1955-56 | Cienfuegos | Oscar Rodriguez |
| 1956-57 | Marianao | Napoleon Reyes |
| 1957-58 | Marianao | Napoleon Reyes |
| 1958-59 | Almendares | Clemente Carrera |
| 1959-60 | Cienfuegos | Tony Castano |
| 1960-61 | Cienfuegos | Tony Castano |