Arsenal will play seven-time winners AC Milan in the pick of the Champions League last-16 draw.
Chelsea will also travel to Italy after the Blues were drawn against Napoli, who qualified for the last-16 for the first time.
Both Arsenal and Chelsea topped their groups, meaning they will have home advantage in the second leg.
Arsenal club secretary David Miles said his side's double-header against AC Milan was undoubtedly the "tie of the round" but admitted the Gunners would have preferred to avoid the Italians.
"It's probably the pick of the round," Miles told the BBC. "They'll be two fantastic games. If I'm being honest, there are some other teams I would have preferred.
"Last time we [Arsenal] played them in season '07-08, we actually went through after winning 2-0 in the San Siro so our recent history against them is good."
Chelsea, the 2008 finalists in Moscow, face a tricky tie against Napoli. The Italians advanced to the last-16 at the expense of Manchester City and will be confident of inflicting further heartache on Andre Villas-Boas when the two sides meet in February.
Chelsea club secretary David Barnard said he was relishing the trip to Italy and insisted Villas-Boas would not be overawed by the occasion.
"It will be difficult," Barnard told the BBC. "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 manager] Andre [Villas-Boas] has experience with Inter [Milan] so he will know the ins and outs of Napoli I'm sure.
"It will be an occasion. It will be a lot warmer, too as we could have got a Russian team where it would have been colder."