Tottenham and Arsenal have the toughest tasks on paper but none of the four English clubs has an easy ride
Milan v Tottenham Hotspur
The seven-times winners will not be relishing the prospect of a second leg at White Hart Lane, and Tottenham will take great heart if they can progress past this one. Milan have revived their fortunes and have a clear lead in Serie A, using their experienced players to great effect, but they may struggle to match the athleticism of Spurs. Incredibly, Filippo Inzaghi is now 37 but can still sneak a goal in his infrequent appearances. More dangerous up front will be the erratic Swede Zlatan Ibrahimovic, above. The Brazilian Pato, soon to return from injury, tends to run with the ball from deeper areas but is still truly to live up to his massive potential. In the centre of the field they have nous and combativeness with Massimo Ambrosini, Andrea Pirlo, Gennaro Gattuso and the evergreen Clarence Seedorf, while Ignazio Abate will have the task of quelling Gareth Bale. Many considered this Milan side to be ageing and over the hill two seasons ago, but Tottenham will respect them; they will need to sit tight in the first leg and rely on the advantage of the atmospheric White Hart Lane in the return.
The view from Italy
Italy breathes a sigh of relief. And understands that Uefa's bowl for the Champions League last 16 draw this time can be benign. Out immediately comes Milan, coupled with Tottenham, the most beatable of the English opponents. Il Giornale
How they qualified
Milan 2nd in Group G P6 W2 D2 L2 F7 A7
Spurs 1st in Group A P6 W3 D2 L1 F18 A11
League position: Milan 1st Spurs 5th
Tournament odds: Milan 22/1 Spurs 25/1
Previous meetings: Never met in the Champions League
FC Copenhagen v Chelsea
Copenhagen are no mean opponents at home, where they held Barcelona this season and beat Manchester United when they were last in the Champions League group stage, in 2006. In getting past that stage this year they have played 10 games, coming through the qualifiers, and are well clear of passive opponents in their domestic league. One cannot ignore the advantage gained in the group stage over wealthy Rubin Kazan and the Greeks, Panathinaikos, but they have the problem of playing the game in February, when their domestic season is on hold. The hub of Chelsea's team, Frank Lampard, right, and Michael Essien, need to regain fitness and form for the new year, but one cannot look beyond Chelsea. They will relish the short trip to meet Stale Solbakken's side. The erratic former Chelsea winger Jesper Gronkjaer, above, will renew friendships, and the Senegalese forward Dame N'Doye could be a danger. The player who is attracting most attention is the experienced Czech Zdenek Pospech, but there is not a single member of the Copenhagen side who Chelsea would ever consider purchasing – a fair barometer. This game looks like a stepping-stone towards Roman Abramovich's so-far elusive and persistent European dream.
The view from Denmark
Can we play this game now? FC Copenhagen will not be able to match Chelsea's pace after the long winter break. However, it is hard to imagine that the Danish champions will be completely run over. They are too tactically sound and physically strong for that to happen. Ekstra Bladet
How they qualified Copenhagen 2nd in Group D P6 W3 D1 L2 F7 A5
Chelsea 1st in Group F P6 W5 D0 L1 F14 A4
League position: Copenhagen 1st Chelsea 4th
Tournament odds Copenhagen 200/1 Chelsea 4/1
Previous meetings: Never met in the Champions League
Marseille v Manchester United
Didier Deschamps is proving a successful leader at the Stade Vélodrome, which is an intimidating venue from which Marseille will need to take an advantage to Old Trafford. Chelsea had little difficulty getting past the French side in their group, although with an under-strength team they lost to a late goal in Marseille, and Manchester United should dispose of them comfortably. They are not to be underestimated, and United fans with long memories will remember a 1-0 defeat on their only previous visit in 1999. The French side are pacy and carry a danger down the left, side where Taye Taiwo has some power. Sir Alex Ferguson will be reunited with his former defender Gabriel Heinze, above, who is very strong in the air. Up front the striker Loïc Rémy is fancied by several European clubs but around him there is a lack of creativity to disturb the defensive rock of Rio Ferdinand and the reliable Nemanja Vidic. Ferguson is integrating and progressing younger players with his usual shrewdness and one eye on the future. Quite smoothly, Rafael, Anderson and Nani are establishing themselves as replacements for Gary Neville, Paul Scholes, and Ryan Giggs, as these three players enter the twilight of their careers.
The view from France
This is certainly a tricky assignment for OM. However, though Manchester United dominated their group they were not up to their usual standard … so, even if things didn't go well at the Vélodrome, OM would still have hope going to Old Trafford. La Provence
How they qualified Marseille 2nd in Group F P6 W4 D0 L2 F12 A3
Man Utd 1st in Group C P6 W4 D2 L0 F7 A1
League position: Marseille 5th Man Utd 1st
Tournament odds: Marseille 100/1 Man Utd 6/1
Previous meetings: Marseille wins 1 Man Utd wins 1 Draws 0
Arsenal v Barcelona
Anyone who witnessed Barcelona's mesmerising first 30 minutes at the Emirates last season, when they eliminated Arsenal in the quarter-finals, will be thirsting to see the tie of the round. How will Arsenal cope, knowing Barca never "park the bus" in first legs? Last time, Theo Walcott hinted at being a threat while the new-boy Marouane Chamakh will present a fresh challenge, attacking crosses against the uncompromising Carles Puyol and the tall Gerard Piqué. However, Arsenal will need Thomas Vermaelen to return, and the power of Abou Diaby to complement Cesc Fábregas, who will be determined to shine against Xavi and Andres Iniesta. Regardless of Lionel Messi's individual brilliance, above, it is Sergio Busquets who needs to be put under pressure as he instigates attacks from deep areas: in the first half at the Emirates last season, he dictated the tempo. Even with Robin van Persie and Fábregas on form, and both Vermaelen and Diaby recovered from injury, it looks a tie too far. However, Arsenal certainly will not lack motivation as they seek revenge for their elimination last season Everyone will wish Arsene Wenger and his team well.
The view from Spain
For the first time, Cesc will be able to play against Barcelona at Camp Nou. This tie comes too soon but will be brilliant. The first 45 minutes from Barcelona at the Emirates were a work of art ... this is a sensational match-up. El Mundo Deportivo
How they qualified Arsenal 2nd in Group H P6 W4 D0 L2 F18 A7
Barcelona 1st in Group D P6 W4 D2 L0 F14 A3
League position: Arsenal 2nd Barcelona 1st
Tournament odds: Arsenal 25/1 Barcelona 5/2
Previous meetings: Arsenal wins 0 Barcelona wins 3 Draws 2