Chelsea vs. Milan: Titles Won by Year
Who won the most tournaments in each year, Milan from Italy or Chelsea from England? Explore a timeline with detailed, side-by-side, international and domestic trophies earned by each of these teams throughout their history, year by year.
By taking a look at the year-by-year history of these two teams, one can see that for both the longest streak of years winning at least one trophy is 3 consecutive years. Chelsea did it (2 times) while Milan did it 3 times.
In terms of years without a title, the worst run of the two is owned by Chelsea, who failed to win trophies for 50 consecutive years (between 1905 and 1954), a streak 7 years longer than the worst streak of Milan, which couldn't won for 43 consecutive years (between 1908 and 1950).
Titles Won Summary: | |
 Chelsea (England) |  Milan (Italy) |
 11 international titles | 18 international titles |
 25 domestic titles |  32 domestic titles |
Titles Year by Year: | ||||
 Chelsea |  Milan | |||
2025 | ||||
| - | |||
- |
| |||
2024 | ||||
| - | - | |||
2023 | ||||
| - | - | |||
2022 | ||||
| - | |||
- |
| |||
2021 | ||||
| - | |||
2020 | ||||
| - | - | |||
Chelsea | Milan | |||
2019 | ||||
| - | |||
2018 | ||||
| - | |||
2017 | ||||
| - | |||
2016 | ||||
- |
| |||
2015 | ||||
| - | |||
2014 | ||||
| - | - | |||
2013 | ||||
| - | |||
2012 | ||||
| - | |||
| - | |||
2011 | ||||
- |
| |||
2010 | ||||
| - | |||
Chelsea | Milan | |||
2009 | ||||
| - | |||
2008 | ||||
| - | - | |||
2007 | ||||
- |
| |||
| - | |||
2006 | ||||
| - | |||
2005 | ||||
| - | |||
2004 | ||||
- |
| |||
2003 | ||||
- |
| |||
- |
| |||
2002 | ||||
| - | - | |||
2001 | ||||
| - | - | |||
2000 | ||||
| - | |||
Chelsea | Milan | |||
1999 | ||||
- |
| |||
1998 | ||||
| - | |||
| - | |||
1997 | ||||
| - | |||
1996 | ||||
- |
| |||
1995 | ||||
| - | - | |||
1994 | ||||
- |
| |||
- |
| |||
1993 | ||||
- |
| |||
1992 | ||||
- |
| |||
1991 | ||||
| - | - | |||
1990 | ||||
- |
| |||
| - | |||
Chelsea | Milan | |||
1989 | ||||
- |
| |||
1988 | ||||
- |
| |||
1987 | ||||
| - | - | |||
1986 | ||||
| - | |||
1985 | ||||
| - | - | |||
1984 | ||||
| - | - | |||
1983 | ||||
| - | - | |||
1982 | ||||
| - | - | |||
1981 | ||||
| - | - | |||
1980 | ||||
| - | - | |||
Chelsea | Milan | |||
1979 | ||||
- |
| |||
1978 | ||||
| - | - | |||
1977 | ||||
- |
| |||
1976 | ||||
| - | - | |||
1975 | ||||
| - | - | |||
1974 | ||||
| - | - | |||
1973 | ||||
- |
| |||
- |
| |||
1972 | ||||
- |
| |||
1971 | ||||
| - | |||
1970 | ||||
| - | |||
Chelsea | Milan | |||
1969 | ||||
- |
| |||
1968 | ||||
- |
| |||
- |
| |||
1967 | ||||
- |
| |||
1966 | ||||
| - | - | |||
1965 | ||||
| - | |||
1964 | ||||
| - | - | |||
1963 | ||||
- |
| |||
1962 | ||||
- |
| |||
1961 | ||||
| - | - | |||
1960 | ||||
| - | - | |||
Chelsea | Milan | |||
1959 | ||||
- |
| |||
1958 | ||||
| - | - | |||
1957 | ||||
- |
| |||
1956 | ||||
| - | - | |||
1955 | ||||
|
| |||
1954 | ||||
| - | - | |||
1953 | ||||
| - | - | |||
1952 | ||||
| - | - | |||
1951 | ||||
- |
| |||
1950 | ||||
| - | - | |||
Chelsea | Milan | |||
1909 | ||||
| - | - | |||
1908 | ||||
| - | - | |||
1907 | ||||
- |
| |||
1906 | ||||
- |
| |||
1905 | ||||
| - (team foundation year) | - | |||
1904 | ||||
| - | - | |||
1903 | ||||
| - | - | |||
1902 | ||||
| - | - | |||
1901 | ||||
- |
| |||
1900 | ||||
| - | - | |||