Arsenal must overcome Barcelona in the last 16 of the UEFA Champions League and Tottenham face another trip to Milan, but the draw has been kinder to Manchester United and Chelsea.
Carlo Ancelotti's side will be strong favourites to see off Copenhagen, while the Red Devils were pitted against Marseille in Friday's eagerly-awaited draw in Nyon.
Arsenal have paid the price for not securing first place in their group, despite winning their opening three fixtures, with a second-round tie against tournament favourites Barcelona.
The two sides locked horns at the quarter-final stage last season and it was Barca who emerged triumphant courtesy of a 6-3 aggregate victory after a dazzling second-leg performance.
Pep Guardiola's men did not go on to lift the trophy but they have started the new campaign in stunning form and Arsenal face a huge challenge if they are to make it through to the last eight.
Tottenham's maiden Champions League adventure continues with a return to the San Siro, this time to play AC Milan.
Spurs were beaten 4-3 by city rivals Inter during the group phase but claimed a thrilling, Gareth Bale-inspired victory in the return fixture at White Hart Lane to help them top the table.
And Harry Redknapp will be in confident mood ahead of the clash even though AC Milan have performed well this term and currently top Serie A.
Elusive
Chelsea enjoyed a straightforward passage through the group stage and their search for an elusive Champions League crown now takes them to Denmark to face Copenhagen.
The Blues' season has taken a turn for the worse in recent weeks but they will fancy their chances of advancing in the competition and reaching the final at Wembley in May.
French champions Marseille finished behind Chelsea and now face another English examination in the shape of Manchester United, who have only lost one game in all competitions this season.
The Red Devils have been impressive in Europe this term and, like all group winners, have the advantage of playing the second leg of their tie at home.
There are some other eye-catching clashes, with defending champions Inter Milan to play Bayern Munich in a repeat of last season's final.
Shakhtar Donetsk, who pipped Arsenal to top spot in Group H, meet Roma, while Valencia do battle with Schalke and Jose Mourinho takes his Real Madrid side to Lyon.
Champions League last 16 draw:
Roma v Shakhtar Donetsk
AC Milan v Tottenham
Valencia v Schalke
Inter Milan v Bayern Munich
Lyon v Real Madrid
Arsenal v Barcelona
Marseille v Manchester United
Copenhagen v Chelsea
First legs to be played on 15/16 and 22/23 February
Second legs to be played on 8/9 and 15/16 March
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