Napoli will take on Arsenal in the Europa League quarter-finals, prior to a possible last-four tie with Villarreal or Valencia.
Napoli reached the quarter-finals by the skin of their teeth after a 3-1 defeat to Red Bull Salzburg on Thursday, their progress owed to a 3-0 win in the first leg.
The Partenopei one and only conquest in the competition came all the back in 1989, when Argentine icon Diego Maradona was still at the club.
Arsenal edged them out on goal difference to qualify for the Champions League Round of 16 during the 2013-14 campaign, although Carlo Ancelotti’s side did win 2-0 in their second group game against the Gunners.
Napoli will contest the first leg away from home due to a UEFA ruling that prevents clubs from the same city playing at home on the same night or consecutive nights.
As Maurizio Sarri’s Chelsea won the FA Cup last season, they have the benefit of playing away to Slavia Prague in the first leg of their tie.
If Napoli pull through their quarter-final, awaiting them in the final four will be Valencia or Villarreal, who knocked out the southerners at the last-16 stage three years ago.
The first legs will be played on April 11, with the return games scheduled for a week later.
Europa League quarter-final draw
Arsenal v Napoli
Villarreal v Valencia
Benfica v Eintracht Frankfurt
Slavia Prague v Chelsea