| AS Roma | v | Shakhtar Donetsk |
| AC Milan | v | Tottenham Hotspur |
| Valencia | v | FC Schalke |
| Inter Milan | v | Bayern Munich |
| Lyon | v | Real Madrid |
| Arsenal | v | Barcelona |
| Marseille | v | Manchester United |
| Copenhagen | v | Chelsea |
| AS Roma | v | Shakhtar Donetsk |
| AC Milan | v | Tottenham Hotspur |
| Valencia | v | FC Schalke |
| Inter Milan | v | Bayern Munich |
| Lyon | v | Real Madrid |
| Arsenal | v | Barcelona |
| Marseille | v | Manchester United |
| Copenhagen | v | Chelsea |
Tottenham will face Italian giants AC Milan in the Champions League last 16, while Arsenal have been drawn with 2009 winners Barcelona.
Manchester United meet Marseille, while Chelsea were handed arguably the easiest tie of all four English clubs as they were handed an appointment with FC Copenhagen.
Arsenal surely face the stiffest task after they were drawn against Spanish champions Barca.
The Catalans eliminated the Gunners in the quarter-finals last season thanks to a virtuoso display by Lionel Messi and are the bookmakers' European Cup favourites again following last month's 5-0 thrashing of Real Madrid.
Spurs, top scorers in the group stage, also face a tough test, against Milan, in their first experience of the knockout stages of the Champions League.
Milan are currently six points clear at the top of Serie A and with plenty of big-match experience in their ranks.
Chelsea were given arguably the kindest draw of the round, up against Danish champions Copenhagen, while Manchester United will play French champions Marseille.
The other ties see Lyon take on Jose Mourinho's Real Madrid, holders Inter, now managed by Rafa Benitez, will face Bayern Munich in a repeat of last season's Bernabeu final, Valencia will play Schalke and Roma have to overcome Shakhtar Donetsk.
Spurs have already beaten holders Inter in the group stage and manager Harry Redknapp was quietly confident about being drawn against AC Milan.
Redknapp said: "It will be a great game. I would have taken AC Milan before the draw. They are leading the league in Italy but it has the makings of a great game over two legs. I'm looking forward to it."
Asked if the experience of the San Siro was an advantage, he replied: "No. They are different players. It would be a fantastic occasion. It is not the worst draw for me. A tough draw but it will be a great game. That's what you want. Great games."
He insisted his side, who have 10 matches domestically before Europe resumes, would be concentrating on the Premier League.
"It's a way off," added Redknapp. "We can put it to one side and concentrate on the league for now.
"It's fantastic for us to be involved in the Champions League. Our first dream was to get into it. To make the group stage was great.
"Then to win the group in possibly the hardest group of all was fantastic."
Spurs were beaten 4-3 by Inter in Italy but came back from 4-0 down thanks to a brilliant hat-trick by Gareth Bale. They then beat Benitez's side 3-1 at White Hart Lane.
The draw for the last 16 of the Champions League is:
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
FC Copenhagen v Chelsea
The first legs will be played on February 15-16/22-23, with the second legs on March 8-9/15-16.