Real Madrid’s trip down memory lane, history repeating for Arsenal: UCL last-16 draw analysis

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Following Monday’s Uefa Champions League last-16 draw, Ian Hawkey breaks down each match-up and predicts which team will progress to the quarter-finals.

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Manchester City v Monaco

Having been thumped the past two weekends by, firstly the 2015 and then the 2016 champions of England, Manchester City might be relieved to have avoided, say, the champions of Italy in a competition their wealthy owners are determined to make a big impression in. But, steady. A City defence that has lately looked tissue-thin against efficient counter-attacking cannot be at all blasé about taking on a Monaco team with a crop of confident, quick young players and an eye-catching glut of goals in domestic competition. Already in Ligue 1 this season, Monaco have racked up more than 50. Already in Europe, they have effectively knocked out one English club, twice beating Tottenham Hotspur in a group they topped.

A poignant tie for Yaya Toure, once of Monaco, if that is, City plan on keeping him and registering him for the Champions League after January.

Winners: Manchester City

Real Madrid v Napoli

Stand by for some nostalgia. Within minutes of Real Madrid and Napoli being paired, the Madrid director Emilio Butragueno was being led by reporters nearly 30 years down memory lane, to when he was a decisive centre-forward for a Madrid side who met and beat a Napoli team freshly crowned Serie A champions, with Diego Maradona in the line-up, in the first round of the 1987/88 European Cup. “The atmosphere,” Butragueno noted of the Naples leg, “was very difficult for us.” A raucous San Paolo is still a great alibi for Napoli, and the visit there of the defending European champions will be noisy and intimidating as long as Napoli have left the Spanish capital after the first leg with a chance of progress against a Madrid with an unbeaten record right now of 34 matches. A fixture to relish for Napoli’s influential former Madrid players, Jose Callejon and Raul Albiol.

Winners: Real Madrid

Benfica v Borussia Dortmund

Thomas Tuchel’s Dortmund anticipate trips to Portugal with optimism. They defeated Sporting in Lisbon and in Germany in this season’s group phase, and they beat Porto away and home in the Europa League earlier this year. Emboldened by topping their group, they have the tag of narrow favourites against Benfica, albeit that the Portuguese champions gave Bayern Munich a stern test in the last-eight of the last Champions League. Tuchel’s concerns will surround how fatigued Dortmund’s leading goalscorer Pierre-Emerick Aubamayeng feels come February, after competing in an Africa Cup of Nations where he will be the figurehead for host country, Gabon. His goals are important, though Dortmund’s high-energy game means goals can be found anywhere across the front line. They scored 21 times in the group phase.

Winners: Dortmund

Bayern Munich v Arsenal

It is beginning to look as if Arsenal against Bayern is an obligatory fixture in the Champions League. If, last season, their pairing in the group phase rather than in the knockouts at least protected the London club from what had become a routine elimination at the hands of the serial Bundesliga winners, a third collision in four years at the last 16 phase will have drawn a weary groan from the Emirates stadium. Bayern may be less domineering in the early months of Carlo Ancelotti’s stint as manager, but precedents are weighty. Bayern are habitual semi-finalists; Arsenal have fallen a round short of the quarters for six successive seasons. And Arsenal’s last visit to the Allianz ended 5-1 in Bayern’s favour. Arsenal’s best hopes rest on Alexis Sanchez retaining into February and March his current pizzazz and Bayern’s defence continuing to show recent symptoms of fragility.

Winners: Bayern

Porto v Juventus

It is one of the most enduring duels of the modern era, informed by huge mutual respect and an enormous vat of experience. Iker Casillas, Porto’s goalkeeper and formerly the captain of Real Madrid, is in the knockout phase of a competition he has won four times for the 17th time in 18 years as a senior professional. At 35, he will still be four years the junior of his long-time rival as the world’s No 1 gloveman, Gigi Buffon, Juventus great, keeper and captain, when they have their latest, high-stakes meeting in February. Casillas against Buffon. It’s been played out in epic Italy against Spain games, and in the colours of Juventus and Madrid. It is an intriguing aspect of a tie that may have an altered complexion if Porto feel the need to sell players to ease heavy debts in the winter transfer window. Juventus, with several veterans, including Buffon, in the side, have targeted winning this competition as a matter of urgency, sensing that time for the Buffon generation may be running out.

Winners: Juventus

Bayer Leverkusen v Atletico Madrid

Diego Simeone’s Atletico Madrid have established a useful habit of negotiating their way past Germany’s finest. Clubs from the Primera Liga traditionally have a bit of a phobia about Bundesliga opponents, but not Simeone’s men, having eliminated Bayern Munich in the Champions League semi-finals last season and then topping a group including Bayern. If any club is entitled to believe the Champions League owes them a gold medal, it is Atletico, twice losing finalists in the last three years. Leverkusen can turn on some vibrant attacking displays but they will up against a famously stoic defence. For the connoisseur of the imaginative set-piece, there should be plenty to study in the course of the 180 minutes, from the skilled dead-ball delivery of Leverkusen’s Hakan Chahanoglu to the well-drilled manoeuvres of Atletico inside the opposition penalty box when corners or free-kicks are launched.

Winners: Atletico Madrid

Paris Saint-Germain v Barcelona

A couple of years ago, on their way to the most recent of their four European Cup victories since 2006, Barcelona firmly put an ambitious, well-funded Paris Saint-Germain in their place, with a 5-1 aggregate win in the quarter-finals of the Champions League. The likes of Barcelona, kings of the continent’s establishment-class, continue to look warily at how PSG grow, but will not be too alarmed at developments at the French champions over the last six months. There will be respect, certainly, for Unai Emery, the Spaniard who took over as manager of PSG in the summer, but he has mislaid some of the formulas that made Ligue 1 a cruise for PSG since they came under Qatari ownership and financing. PSG, third in the French top flight, look reliant on Edinson Cavani’s goals and leading of the line. Barca will beware the Uruguayan and the wily campaigner Thiago Motta, who always wants to show the Barcelona he grew up at but left when they were on the cusp of extended greatness, that he can still boss a midfield.

Winners: Barcelona

Sevilla v Leicester City

Not, perhaps, the glamorous, high-profile tie that Leicester City’s supporters had been hoping to decorate their debut campaign in the European Cup with, but there are worse places to have to travel to from a chilly February in the English midlands to than the capital of Andalusia, and a Sevilla with an attacking panache. The Europa League holders may have the better pedigree but as Monchi, their director football, felt the need to remind smiling sevillistas, the Leicester currently 14th in the Premier League “are the champions of England, and have just scored four goals against Manchester City.” Monchi is not alone in believing Leicester are “are focusing on the Champions League,” rather than domestic matters. He will hope that by the time the first leg comes around key Leicester men like the Algerians Riyad Mahrez and Islam Slimani and Ghanaian Daniel Amartey have been focused intensely and for several tiring weeks on the Africa Cup of Nations, which concludes in Gabon just before the last-16 Champions League phase begins.

Winners: Sevilla