50 free AC Milan trivia questions with answers — sports quiz, new questions added Aug 2026.
AC Milan is Italy's most decorated club in Europe: seven European Cups, five UEFA Super Cups and a FIFA Club World Cup, plus 19 Scudetti at home. This quiz walks through the whole story, from an English expatriate founding Milan Foot-Ball and Cricket Club in 1899 to the Swedish Gre-No-Li trio, Nereo Rocco's first European Cup, the Berlusconi years of Sacchi and Capello, and the Pioli side that set a club points record in 2022. Expect questions on the kit, the Derby della Madonnina, the stadium the club built for itself in 1926, record scorers and appearance-makers, famous finals won and lost, and a few left-field facts about the mascot, the anthem and the club's brief spell in motorsport. Fifty questions, four options each, with a short explanation after every answer. Play on your phone, share your score, or print the set for a pub quiz night.
30 of 50 questions with answers and explanations. Play the quiz
Q 01In which year was AC Milan founded?
1899
The club claims 16 December 1899 as its birthday, though records suggest it was a few days later; the charter has been lost.
Q 02Which English expatriate founded Milan Foot-Ball and Cricket Club?
Herbert Kilpin
In honour of its English origins the club kept the English spelling of the city's name rather than the Italian Milano.
Q 03In 1926, Milan moved to which ground, its home for the following century?
San Siro
Before 1926 the club bounced between grounds including the Trotter pitch, later the site of Milan Central railway station.
Q 04Milan's stadium is officially named after which player who represented both Milan clubs?
Giuseppe Meazza
The more familiar name comes from the district in which the stadium stands.
Q 05The Derby della Madonnina takes its name from a statue atop which building?
Milan Cathedral
The first derby was played in the final of the 1908 Chiasso Cup in Switzerland, which Milan won 2–1.
Q 06In how many seasons has Milan played outside Serie A?
2
Both Serie B seasons came in the early 1980s, the first as punishment for the Totonero betting scandal.
Q 07In which year did Silvio Berlusconi buy Milan and save it from bankruptcy?
1986
He appointed rising manager Arrigo Sacchi and signed the Dutch trio of Gullit, van Basten and Rijkaard.
Q 08How many trophies did Milan win during Berlusconi's 31-year tenure?
29
Berlusconi is the club's longest-serving president, with a two-year vacancy between 2004 and 2006 interrupting his reign.
Q 09In which season did Milan become the first team to win Serie A without losing a game?
1991–92
Perugia had gone unbeaten in 1978–79 but finished second; Milan's run was part of a 58-match unbeaten streak.
Q 10Who holds Milan's record for total appearances, with 902 official games?
Paolo Maldini
His 647 Serie A appearances for the club are also an all-time Serie A record.
Q 11How many Italian league titles had Milan won by the end of the 2024–25 season?
19
The first came in 1901, ending a three-year Genoa hegemony, and the most recent in 2022.
Q 12How many European Cup/Champions League titles has Milan won?
7
Only Real Madrid has more; Milan's fifth win in 1994 earned it the right to keep the trophy permanently.
Q 13Milan's first European Cup, in 1963, came after beating which club in the final?
Benfica
Nereo Rocco's side won the Scudetto in 1961–62 and the European Cup the very next season.
Q 14Milan's 1969 European Cup win was a 4–1 final victory over which club?
Q 21After Calciopoli, Milan's points deduction was reduced on appeal to how many?
8
The reduction kept Milan in the Champions League, which it went on to win in 2007.
Q 22Milan beat which Romanian club 4–0 in the 1989 European Cup final?
Steaua București
It was the club's first European Cup in two decades; Milan retained the trophy a year later.
Q 23What nickname did the Italian media give the Milan side of 1988–1990?
The Immortals
A World Soccer magazine poll of experts voted that team the best club side of all time.
Ajax
The club followed up by winning the Intercontinental Cup the same year.
Q 15Which catenaccio pioneer coached Milan to its first European Cup?
Nereo Rocco
He remains the club's longest-serving manager, over nine years across two spells.
Q 16Milan's famous 1950s 'Gre-No-Li' trio came from which country?
Sweden
Gren, Nordahl and Liedholm helped bring the Scudetto to Milan in 1951, 1955, 1957 and 1959.
Q 17Milan's 1956 Latin Cup triumph came against which club?
Athletic Bilbao
Milan's 1951 and 1956 Latin Cup wins are a joint record; the club was also the first Italian side in the European Cup.
Q 18Who is Milan's youngest ever goalscorer, netting in a league match at just 17?
Gianni Rivera
He debuted in 1960 and stayed for 19 seasons, finishing third on the club's all-time scoring list.
Q 19In which year did Milan win its tenth Scudetto, earning the star on its jersey?
1979
The same year Gianni Rivera retired and Franco Baresi played his first full season.
Q 20Which betting scandal saw Milan relegated to Serie B for the first time in 1980?
Totonero
Milan bounced straight back by winning Serie B, then went down again a year later.
Q 24How many Serie A matches did Milan's early-1990s unbeaten run last?
58
It began and ended against Parma, and is the third-longest top-flight run in Europe behind Steaua and Celtic.
Q 25Which club did Capello's Milan beat 4–0 in the 1994 Champions League final?
Barcelona
It is remembered as one of Milan's greatest ever performances, a year after losing the 1993 final.
Q 26Which club beat Milan 1–0 in the 1993 Champions League final?
Marseille
Milan reached three consecutive finals from 1993 to 1995, winning only the middle one.
Q 27Milan beat which club on penalties in the 2003 Champions League final?
Juventus
It was the first Champions League final between two Italian clubs and the only European meeting of the pair.
Q 28Milan led 3–0 at half-time of the 2005 Champions League final but lost to whom?
Liverpool
Milan got revenge two years later, winning the 2007 final 2–1 against the same opponent.
Q 29Carlo Ancelotti left Milan in 2009 to manage which club?
Chelsea
He departed after 420 matches, making him Milan's second-longest-serving manager.
Q 30Whose world transfer record did Kaká's €67 million sale in 2009 break?
Zinedine Zidane
The new record lasted less than a month before Cristiano Ronaldo's £80 million move.