By Ben Lyttleton
December 20, 2012
Sir Alex Ferguson and Cristiano Ronaldo were together from 2003-09 at Manchester United.
Alex Livesey/Getty Images

A dramatic Champions League Round of 16 draw was made Thursday morning in Nyon, Switzerland, giving football lovers exciting matchups to look forward to in February and March. Part of the drama of drawing the eight pairings now comes from not knowing exactly how the teams will be playing when the games come along in eight weeks' time: confidence, injuries and general form could all change the picture between now and then. Not to mention the longer-than-usual three weeks between first and second legs. Here is a breakdown ...

Real Madrid vs. Manchester United\n

This is the highlight of the round featuring, as it does, Cristiano Ronaldo returning to his former club for the first time; also Jose Mourinho up against United, the team against whom he made his name with Porto's Champions League win at this stage of the competition in 2004 (and with whom he has been linked as a possible successor to Sir Alex Ferguson); and the memory of what happened in 2003, when Madrid won a quarterfinal 6-5 on aggregate in a game that, arguably, changed the face of English football forever. Watching the second leg at Old Trafford, a 4-3 United win in which the Brazilian Ronaldo scored a hat trick, was Roman Abramovich, who was reportedly so seduced by the attacking football that he bought Chelsea. (He can't have liked it that much: the first coach he hired who really played an attacking game was Roberto di Matteo this season, and he only lasted three months.)

The difference is that each team has a different priority this season: for United, it has to be wresting the league out of the grasp of its "noisy neighbors" Manchester City. With City out of all European competition, after finishing at the bottom of Madrid's group, that won't be easy. Madrid, on the other hand, have as much as written off La Liga: it is currently 13 back on Barcelona, and president Florentino Perez reportedly told Mourinho that winning a Copa del Rey and Champions League double was his target for the season.

"We have set a clear goal: to win the Champions League," midfielder Sami Khedira told Bild this week. "We aren't doing Real Madrid justice this year. We cannot be happy with the season we are having. We haven't been able to get into the right rhythm since the very beginning."

The chance will come in February, and it will be fascinating to see Ronaldo up against his former teammates. They might be surprised by how much better he has become.

Pick: Real Madrid

AC Milan vs. Barcelona

What a week it's been at Barcelona: on Sunday night it came from behind to destroy its closest title rival, Atletico Madrid, a 4-1 win. Lionel Messi scored two more goals, taking his tally for 2012 to 90 and within days signed a new contract until 2018, in a deal making him the world's best player. Xavi Hernandez, Carles Puyol and Cristian Tello also extended their deals until 2016, and Eric Abidal rejoined training after his liver transplant nine months ago. Everything was hunky-dory.

Then the awful news, confirmed Wednesday night, that a tumor in coach Tito Vilanova's parotid (salivary) gland had returned, and he would need emergency surgery. That took place Thursday morning, with Jordi Roura, Vilanova's assistant, stepping in to take first-team affairs. Vilanova has done so well as Barcelona boss -- making the team different to Pep Guardiola's side, but even more effective (15 wins and one draw in La Liga has put it on target for another record-breaking season, already nine points ahead of second-place Atletico) -- that the question has been raised about Guardiola's effectiveness in his next job without him. The football world has united in wishing Vilanova a speedy recovery, and we hope he is on the bench in time for the Milan game next February.

Milan coach Massimiliano Allegri has done well to keep his job this season, as at one stage, Milan looked unlikely to qualify from its group. A recent run of form, which started with a league win over Juventus, has pushed it up the Serie A table, and if it keeps confidence between now and February, it could prove a tricky opponent.

That said, the promotion of Roura, who grew up with Vilanova in Barcelona's La Masia, its youth academy, and was given his first-team debut by Johan Cruyff in 1988, is unlikely to affect Barcelona too much. If the assistant's assistant is half as good as the assistant has shown to be, then Barcelona's recent record -- it has reached the semi-final or better in each of the last five seasons -- will be safe.

Pick: Barcelona

Shakhtar Donetsk vs. Borussia Dortmund

This is the battle of the dark horses: Shakhtar was superb in its game against champion Chelsea and would have topped the group (and had an easier Round of 16 draw) had it not conceded a last-minute winner in a 3-2 loss at Stamford Bridge.

The tactical game between the coaches will be fascinating: For Shakhtar, Mircea Lucescu, who shrugged off his Romanian coach of the Year award this week with the brilliant phrase, "I've asked you several times to leave me and try to look at the younger generation of coaches;" and for Dortmund, Jurgen Klopp, who has laughed off talk of a future at Chelsea or Liverpool and claimed that his team, in the next four years, could achieve some truly special things.

The problem for Shakhtar is that, as always, this game comes in the midst of its winter break. It does not have a league game in December through February, so will have to hit the ground running against Dortmund. No easy task. Two of the breakout stars of this campaign -- Henryk Mkhitaryan (Shakhtar) and Marco Reus (Dortmund) -- go head-to-head in what could be the most exciting tie of the round.

Pick: Borussia Dortmund

Arsenal vs. Bayern Munich

The good news for Arsenal: At least it wasn't Barcelona, a team it has drawn twice in the last three years in the competition. The bad news? Bayern is probably the next best side.

Arsenal paid the price for failing to top Group B (which it would have done by beating Olympiakos on Matchday Six) but Bayern, runner-up last May, has a stronger squad this season and goes into Germany's winter break nine points clear at the top of the Bundesliga. A knee injury to center back Holger Badstuber could yet cost Bayern, but there's no doubt it is better than last year, and Arsenal is weaker.

The tie also sees a Munich reunion for Arsenal winger Lukas Podolski, who has at times looked worthy of his status as Arsenal's best-paid player, and at other times, barely merited a place on the bench. He has played well in Europe, though.

Pick: Bayern Munich

Valencia vs. Paris Saint-Germain

Someone has been looking after Carlo Ancelotti in recent weeks. His job was under threat before PSG beat Porto to top a very comfortable Group A, and now the Italian's side faces Valencia, a team that is struggling domestically and which earlier this month fired coach Mauricio Pellegrino.

"If there's any team we want to avoid, it's Madrid," PSG midfielder Blaise Matuidi said.

Valencia has a crop of French players -- among them Adil Rami, Aly Cissokho and Jeremy Mathieu -- and an excellent record against French teams.

"It will be special for me as I have good memories of Valencia," PSG sports director Leonardo, who played for the Spanish club, told beIN Sport. "Playing Madrid would have been fantastic, but I'd rather play them later in the competition: and lots of clubs wouldn't have wanted to play PSG, which is a sign of the progress we are making already." With Lucas Moura soon to join the PSG squad in January, the French side, reported on Thursday to be receiving ?150 million in "funding" from the Qatar Tourism Authority, has to be favored.

Pick: PSG

Galatasaray vs. Schalke

Schalke is the team from Pot 1 (of group winners) that everyone would have wanted to face. Since beating Arsenal at the Emirates on Matchday Five, when it was five points ahead of German champion Borussia Dortmund in the Bundesliga, it has hit a major slump, culminating in coach Huub Stevens losing his job last week. The German press has reported that Di Matteo is a target, as is Mainz 05 boss Thomas Tuchel, but any new man would come in at the end of this season, so youth team coach Jens Keller is holding the fort for now. Lewis Holtby and Klaas-Jan Huntelaar, whose contracts expire at the end of the season, might still be around for this tie, which would give Schalke a huge advantage. Reports in Germany suggested that Stevens' ousting was connected to their contract talks.

For Galatasaray, this is the reward for seeing off Cluj and Braga to finish second in Group H, and the chance for Burak Yilmaz, with six goals in six Euorpean games this season, to continue his remarkable form.

Pick: Schalke

Celtic vs. Juventus

Celtic coach Neil Lennon tweeted after the draw: "Absolute beauty of a tie...very tough but they all potentially were."

Celtic has a decent record against Juventus, winning 1-0 at this stage of the 1982 European Cup (it lost the second leg 0-2), and winning 4-3 at home in the 2001 competition group stage (it lost the away leg 2-3).

But the joy will be greater for Juventus counterpart Antonio Conte, who will see this tie as eminently winnable, even though it comes amid a tough Serie A schedule, against Fiorentina, Roma and Napoli. Juventus topped Chelsea and Shakhtar in its group and is now looking a dangerous contender.

Pick: Juventus

Malaga vs. Porto

With so many big teams facing off against each other, this season's competition could open up for an outsider and the winner of this tie might just be it.

Malaga, a debutant in the Champions League, surprised many by romping to the top spot in Group C and was, along with Porto, the first side to reach the last 16. Coach Manuel Pellegrini was in charge of Villarreal when it reached the 2006 semi-final. Porto has much more of a European pedigree even if this side is very different from Andre Villas-Boas' Europa League winners of 2010. Porto may face January bids for Joao Moutinho and James Rodriguez but is expected to hold onto both players, for now at least.

Pick: Porto

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