Chelsea and Arsenal must both overcome tough Italian tests in the last 16 of the Champions League after yesterday’s draw in Nyon.
The London clubs are the only remaining Barclays Premier League sides in the competition following the exits of Manchester United and Manchester City in the group phase.
But managers Andre Villas-Boas and Arsene Wenger must overcome Serie A opponents if they are to reach the quarter-final stage, with Chelsea drawing Napoli and the Gunners landing AC Milan.
European champions Barcelona were handed a meeting with Bayer Leverkusen, currently sixth in the German league.
Barca’s arch-rivals Real Madrid will also be satisfied after pulling out CSKA Moscow.
Bayern Munich, who will host the final at their Allianz Arena, were paired with Basel while 2010 champions Inter Milan will face Marseille.
Zenit St Petersburg take on Benfica and Lyon were pulled out against last 16 surprises APOEL Nicosia.
Manchester City and Manchester United will both face difficult matches in the last 32 of the Europa League after Roberto Mancini’s side drew holders Porto and their neighbours were paired with fellow Champions League dropouts Ajax. Stoke City have been drawn against Spanish side Valencia.
Manager Andre Villas-Boas feels Chelsea have been handed “one of the most difficult draws” after being paired with Napoli in the Champions League.
Napoli took four points off Manchester City in Group A to edge Mancini’s side out of the competition, and their forward pairing of Edinson Cavani and Ezequiel Lavezzi is one of the most feared in Europe.
Blues boss Villas-Boas knows all about the threat posed by Napoli from his time working under Jose Mourinho at Inter Milan.
“I think we have one of the most difficult draws, but whichever team you get in the last 16 will be a difficult team,” Villas-Boas said.
“Napoli is a club that represents the city and the city has great empathy with the club. It has a tremendous fan base and it is one of the most difficult and exciting games of the last 16, no doubt about it.
“They are a side that works collectively very well and (Napoli coach) Walter Mazzarri has always been a coach that organises his teams very well.
“They have been improving tremendously under his guidance and have been gaining the results that they want and they expect.
“They are fully motivated and they have a lot of talent coming through like (Marek) Hamsik and (Edinson) Cavani. They have a lot of talent throughout.
“We are looking forward to the games and hopefully we can prepare well and hopefully we can go through.”
Wenger, meanwhile, has challenged his Arsenal squad to maintain their momentum to give themselves every chance of knocking out AC Milan, who were runners-up to Barcelona in their group.
Arsenal beat AC Milan 2-0 away at the same stage of the competition in 2008 as they progressed to the quarter-finals.
“It is a difficult draw, but an exciting one, and they could say exactly the same thing I suppose. It is a 50-50,” Wenger said.
“Ideally, it is a draw for one round later, but you take them when they happen.
“Everybody knows Milan, everybody knows Arsenal. We have been in the Champions League for many years and both sides play positive football.”
Wenger added: “Let’s make sure we continue to improve until February. Then we can take our chance with full power and belief.”
Milan were knocked out of last season’s competition at the last 16 stage by Tottenham.
Manchester City manager Mancini is preparing for a Europa League outing which “feels like a Champions League game” after his side’s drop into the secondary continental competition.
City were paired with reigning champions Porto, who also won the 2004 Champions League, and will travel for the first leg before a return fixture at the Etihad Stadium.
“Manchester City against Porto feels like a Champions League game, it is probably the toughest game we could have had,” he said.
He added: “It will be a hard match for us. We know this game will be difficult, but also it will be difficult for them. It is a good game for the fans, a big team coming to Manchester, and we will be looking forward to it.”
City and Ajax both found themselves in the Europa draw after being edged out of hard groups – City finishing behind Bayern Munich and Napoli and the Dutch side missing out to Lyon and Real Madrid.
Both United and Porto, though, were bettered by less fancied opposition, with Sir Alex Ferguson’s side third behind Basel and Benfica and the Portuguese club edged by Apoel Nicosia and Zenit St Petersburg.
After the draw in Nyon, Ferguson joined defender Chris Smalling in welcoming the meeting with Ajax, with the first leg at the Amsterdam ArenA. He said: “I have never played them before in competitive football in my managerial career. They are a good team and we are looking forward to it.”
Smalling added: “(Exiting the Champions League) was a massive disappointment, but then you look at the calibre of teams that are in there (Europa League).
“We have drawn Ajax, they have a lot of history. That will be a good test. If you are in there, a lot of the teams will be kicking on. Whoever wins the competition will be a good team.”
Another of the big-name Champions League fallers, Valencia, will face Stoke, with the first leg at the Britannia Stadium.
Lazio meet Atletico Madrid in another eye-catching fixture.