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| Arsene Wenger took Arsenal to the Champions League final in 2006 |
Arsenal and Chelsea, the only remaining English sides in the competition, both face first legs in Italy.
Defending champions Barcelona face German side Bayer Leverkusen.
The first legs will take place on 14/15 or 21/22 February, while the return fixtures are scheduled for 6/7 or 13/14 March.
Arsenal travel to Milan for the first leg on 15 February, before playing the second leg at Emirates Stadium on 6 March.
Chelsea go to Naples on 21 February with the return leg scheduled for 14 March.
Real Madrid, who have won the tournament nine times, face CSKA Moscow while Basel, whose defeat of Manchester United in the final round of group games knocked the English side out, will play four-time winners Bayern Munich.
Inter Milan, who beat Bayern Munich 2-0 to win the competition in 2010, face French side Marseille while Lyon host Cypriot side Apoel who are making their first appearance in the knockout stages.
Chelsea will be wary of Napoli, who currently lie fifth in Serie A, as the Italian side were responsible for Manchester City's exit, taking four points off Roberto Mancini's side in Group A.
"It will be difficult," said Chelsea club secretary David Barnard. "Napoli were in the same group as Man City and Man City are unfortunately no longer with us so that has some bearing on quality of Napoli.
"We all know that [Chelsea boss] Andre [Villas-Boas] has experience with Inter [Milan] so he will know the ins and outs of Napoli I'm sure.
"It will be a lot warmer, too as we could have got a Russian team where it would have been colder."
Arsenal, who have been knocked out by Barcelona in the last two seasons, will take the confidence from a 2-0 quarter-final victory over AC Milan at the San Siro three years ago when they face the Italians in the last eight.
"It's probably the pick of the round," said Arsenal club secretary David Miles. "There were probably other teams we would have preferred but the last time we played them in the knockout stage, in 07-08, we actually went through and won 2-0 in the San Siro."
"We also knocked out, in fairly recent history, Roma and Inter Milan. It's going to be tough. Everyone has earned the right to get to this stage but nevertheless, we're confident and it's going to be two great games.
"Having been on the rough end of Barcelona for two years running, it's nice to know it couldn't happen a third time. It's a good draw for us."
AC Milan director Umberto Gandini added that he felt his side are in better shape compared to their last meeting.
"We've got to break tradition, last time [we played Arsenal] we were knocked out, losing 2-0 the San Siro," said Gandini. "But it's an exciting fixture and we are determined to go through.
"I think if you had the game today maybe Arsenal is not in the greatest condition and we are in a better status. But in two months things may change.
"They are rebuilding in a certain way but are still very, very dangerous.
"It's very important we play well in Milan and very important we come back to London in good shape. We are AC Milan. They are Arsenal. It is a great match."
CHAMPIONS LEAGUE LAST 16 DRAW:
Lyon (Fra) v APOEL (Cyp)
Napoli (Ita) v Chelsea (Eng)
AC Milan (Ita) v Arsenal (Eng)
Basel (Swi) v Bayern Munich (Ger)
Bayer Leverkusen (Ger) v Barcelona (Spa)
CSKA Moscow (Rus) v Real Madrid (Spa)
Zenit St Petersburg (Rus) v Benfica (Por)
Marseille (Fra) v Inter Milan (Ita)
