Milan qualified for the last 16 stage as runners-up in Group G behind Real Madrid and, with a strong attacking unit, they will aspire to repeat their performance of 2006-07 in which they defeated Liverpool in the final to lift the Champions League.
On paper the Italian giants are the overwhelming favourites for this fixture. With their rich history combined with European experience and fearsome strikeforce upfront, Milan will be confident of seeing off the challenge of Champions League debutants Tottenham Hotspur over the two legs in this last 16 tie.
However, having watched their city rivals and defending Italian and European champions Inter almost capitulate to Spurs at San Siro in a group stage game earlier this season, Diavolo coach Massimiliano Allegri is not taking the risk of dismissing Spurs even though Inter's nemesis Gareth Bale is out injured of tonight's clash.
“It doesn't matter if Bale doesn't play because Tottenham have done well recently without him,” warns Allegri. “They are a tough side, very well organised with a good team spirit. Some of their players have real quality.
“The best teams are in this competition, so from now on we can't afford to make any mistakes or we will be eliminated. In the last two seasons Milan were eliminated by English sides so we have to be careful. Statistics mean nothing to me now and I think that my team have a great chance to qualify for the quarter-finals.”
Star striker Zlatan Ibrahimovic is more positive, and enthuses: "The experience that Milan have in Europe makes the difference. It's an advantage for me – many of the players here have won the Champions League and this gives confidence to us all.”
Completing The Italian Job
Tottenham Hotspur return to the scene of one of their finest second half performances in history as they are back in Milan, this time to confront the Rossoneri. In the group stage of the Champions League this season, the London-based club shook Inter to the core. After going 4-0 down at the break, they staged a scintillating near-comeback spearheaded by Gareth Bale to eventually reduce the deficit to 4-3.
Back at San Siro, Harry Redknapp's team will hope to invoke the spirits of that great night and pull off a coup against Milan tonight. The manager says that his players are enjoying the European stage and is hopeful of stretching the adventure further.
“The atmosphere in these international competitions is always very good, and we already proved that we can do well in Europe,” enthuses Redknapp. “We have a few players out, but Milan also have some injured players.
"Tottenham are writing a beautiful story this term in the Champions League, it's another level of football. The Premier League is a great league but this atmosphere is really wonderful, especially for the supporters.”
Spurs have scored 18 goals in six group stage matches in the Champions League this campaign but have also conceded more than they should have. However, the Premier League side will be emboldened by the fact that Milan have won none of their past five matches in European competition against English opposition and have been eliminated at this stage by English teams in the last two seasons.
TEAM NEWS
Milan
January signings Urby Emanuelson, Mark van Bommel and Antonio Cassano are ineligible to play in the Champions League for Milan having already featured in the competition with their respective former clubs.
Captain Massimo Ambrosini is out with a thigh problem, Andrea Pirlo has a knee injury and Kevin-Prince Boateng is suffering from an Achilles problem. Gianluca Zambrotta is unavailable as well.
Regular centre-back Thiago Silva could be moved to the midfield with Mario Yepes replacing him at the heart of the defence and playing alongside Alessandro Nesta, who like Nicola Legrottaglie, Ignazio Abate, Luca Antonini and Marco Amelia have recovered from injury.
Tottenham Hotspur
Wingback Gareth Bale is out of the fixture but Rafael van der Vaart has been passed fit to feature against Milan. Luka Modric has travelled to Italy but remains a doubt as he had his appendix removed just under a fortnight back.
Peter Crouch too is doubtful with a back injury and will face a late fitness test. Younes Kaboul, Ledley King and Tom Huddlestone are long-term injury concerns while Jermaine Jenas is suspended.
Prediction
Tottenham Hotspur have shown that they are not afraid of taking on the big guns and in Milan tonight the Premier League club will attempt to showcase their calibre. However, the Rossoneri will have home advantage and given their return to winning ways they will eke out a victory. Spurs, though, could get a valuable away goal.
Milan 2-1 Tottenham 
