Jose Mourinho's Inter will play holders Manchester United, Claudio Ranieri will take his Juventus side back to former club Chelsea and, Roma have to negotiate past Arsenal to get closer to a dream final on home soil.The matches, for a place in the quarter-finals, will be played over two legs on February 24/25 and March 10/11.
Former Chelsea manager Mourinho made it clear that he wanted to draw a top club and he has landed a mouth-watering clash with the English champions, with the first leg to be played at the San Siro.
The tie will revive memories of Mourinho's famous celebration down the touchline at Old Trafford in March 2004 when a last-minute goal sent Porto through and on to eventual victory in the Champions League final.
"I am satisfied, I wanted the best and I have got the European champions who maybe in two days will be World champions," said Mourinho.
"It is a team with the current Ballon D'Or winner (Cristiano Ronaldo), a great coach in Sir Alex Ferguson and a stadium with a fantastic atmosphere.
"It will be unforgettable returning to Manchester. Some say I have a good record against Alex Ferguson but the record isn't mine, it's Porto's and Chelsea's."
Ranieri was another popular figure in the Premier League with Chelsea, before being replaced by Mourinho in 2004, and the Bianconeri coach is looking forward to going back to Stamford Bridge for the opening tie.
"This triple Anglo-Italian challenge is fascinating," said Ranieri. "And from our perspective, we'll try to keep Chelsea off the top of the world where (owner Roman) Abramovich wants to lead them.
"Chelsea are focused on winning the Champions League, for Abramovich it would be a disaster not to win it.
"It's a great challenge. I wouldn't say I'm happy but it will be a fascinating match, we'll need to be on top of our game.
"You cannot forget four years at a club. I don't think Chelsea forget either."
After topping a group that included last years runners-up Chelsea, Roma coach Luciano Spalletti will take his side back to London to face Arsenal at the Emirates Stadium in the first leg.
"That (draw) does me just fine," said Spalletti. "There's no point in talking about it now we must simply show what we're made of and how we're prepared to make sacrifices.
"To Arsenal I want to congratulate them for their system. They have many young players on their way to becoming great players who are being chased by all the big clubs in Europe."
Elsewhere in the draw Spanish giants Barcelona face French champions Lyon, nine-time European champions Real Madrid play five-time winners Liverpool and, four-time champions Bayern Munich entertain Sporting Lisbon.
Atletico Madrid have been paired with FC Porto and Villarreal take on Panathinaikos in the remaining ties.
UEFA Champions League 2008-09
Last 16 First Leg
Tuesday 24 February 2009
Arsenal v Roma (1945)
Atletico Madrid v Porto (1945)
Inter v Manchester United (1945)
Lyon v Barcelona (1945)
Wednesday 25 February 2009
Chelsea v Juventus (1945)
Real Madrid v Liverpool (1945)
Sporting Lisbon v Bayern Munich (1945)
Villarreal v Panathinaikos (1945)
Last 16 Second Leg
Tuesday 10 March 2009
Bayern Munich v Sporting Lisbon (1945)
Juventus v Chelsea (1945)
Liverpool v Real Madrid (1945)
Panathinaikos v Villarreal (1945)
Wednesday 11 March 2009
Barcelona v Lyon (1945)
Manchester United v Inter (1945)
Porto v Atletico Madrid (1945)
Roma v Arsenal (1945)
Source: UEFA
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