The majority of trials have either ended in guilty verdicts being overturned or charges expiring under statute of limitations rules which critics say his lawyers have skilfully exploited.
He has always denied all charges and says he has been unjustly victimised by left-wing judges. Critics say he has used his influence to get off the hook.
Key dates in Berlusconi's courtroom dramas:
1994: Berlusconi is accused of bribing tax police and is sentenced to 33 months in prison. He is acquitted on appeal in 2000 when some of the charges expire.
1995: He is accused of buying a football player for his club AC Milan with a slush fund. The case expired in 2002 thanks to a law passed by his parliamentary majority that decriminalised some false accounting.
1995: Accused of tax fraud in the purchase of a luxury villa near Milan, he again benefits from the charges running out under the statute of limitations.
1995: Berlusconi is accused of fraud in the purchase of the film production company Medusa and sentenced to 16 months in prison. He is acquitted on appeal in 2000.
1995: The tycoon is accused of illegally financing a political party with an offshore fund, All Iberian, and is sentenced to 28 months in prison. He is acquitted in 1999 because of the statute of limitations.
1996: He is accused of fraud in another part of the All Iberian inquiry but is acquitted in 2005.
1998: Berlusconi is accused of bribing judges to promote his business interests but is eventually acquitted by the Court of Cassation in 2007.
2012: He is convicted of tax fraud committed by his media company Mediaset and is sentenced to four years in prison, reduced to one year because of an amnesty, and a five-year ban from holding public office.
March 2013: Berlusconi is sentenced to a year in prison for leaking a police wiretap in one of his newspapers in an attempt to damage a political rival, but the case times out under the statute of limitations.
May 2013: Prosecutors in Naples file charges against Berlusconi for allegedly bribing a left-wing senator in a move that helped bring down prime minister Romano Prodi in 2008.
June 2013: A court in Milan sentences Berlusconi to seven years in prison for abuse of office and having sex with an underage prostitute nicknamed "Ruby the Heart Stealer".
August 2013: Italy's highest court hands Berlusconi his first ever definitive conviction, confirming his one-year prison term for tax fraud.
January 2014: The billionaire is accused of paying off witnesses - young women who attended his famous soirees -- to provide false testimony in the Ruby trial.
February 2014: Berlusconi's trial on charges of senator bribery begins in Naples.
May 2014: The ageing media magnate sees his prison sentence converted to community service in a home for elderly dementia sufferers, which he attends for four hours, once a week, for ten months.
July 2014: An appeals court overturns the guilty verdict in the Ruby case, saying Berlusconi did not know the exotic dancer was 17 at the time.
March 2015: Berlusconi completes his community sentence, which was cut short for good behaviour. Two days later, the Court of Cassation upholds his acquittal in the Ruby case.