The Champions League quarter-finals will include an all Italian fixture in Milan–Napoli while Inter have been drawn against Portuguese side Benfica.
The draw took place at the UEFA headquarters in Nyon on Friday morning.
The first-leg of the quarter-finals will take place on April 11 and 12, with the second legs scheduled for April 18 and 19.
It is the first time that there have been three Italian sides in the last eight of Europe’s flagship competition since 2006.
Milan are the second-most successful side in the history of the competition with seven titles to their name, most recently lifting the trophy in 2007.
For Napoli, this campaign is already their most successful in the club’s history, having never previously reached the last eight of the competition.
With three titles under their belt, Inter are the second-most successful and most recent Italian winners of the competition, having lifted the trophy in 2010 under Jose Mourinho.
The winners of Milan-Napoli and Benfica-Inter will play each other in the semi-finals of the competition, meaning that only one Italian side can possibly make it to the final.
The semi-finals are due to take place on May 9 and 10.
The finalists will meet on June 10 at the Ataturk Olympic Stadium in Istanbul.