Wayne Rooney celebrates after scoring (AFP)

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Milan - Wayne Rooney was the hero as Manchester United made AC Milan look old in a 3-2 win in the Champions League last 16 first leg clash here on Tuesday to record their first ever victory in the San Siro.

Rooney scored a brace as Milan's old legs finally caught up with them as United came from behind to win at a canter until some late drama that saw United's Michael Carrick dismissed in injury time for a second booking.

Ronaldinho gave Milan an early lead but after Paul Scholes's fortuitous equaliser Sir Alex Ferguson's side gradually took control and by the end they threatened to run up a cricket score.

Substitute Clarence Seedorf's clever backheel finish from Ronaldinho's cross five minutes from time was the only thing that gives the Italians hope for the second leg at Old Trafford.

Milan were off to a dream start, taking the lead after only three minutes and appropriately United old boy David Beckham was involved.

His free-kick into the box was only helped on by Patrice Evra and fell kindly to Ronaldinho at the back post who caught it on the volley and a wicked deflection off Carrick took it past a helpless Edwin van der Sar.

That seemed to unsettle United and give Milan wings and on seven minutes Pato broke through the middle and fed Ronaldinho to his left but Van der Sar saved his low shot.

AC Milan were bossing the early action and a surging run from the back from Thiago Silva saw him slip in Luca Antonini on the overlap but he shot wide of the near post.

Ronladinho then tried to win a penalty as he ran at Rio Ferdinand but the referee waved the appeals away.

Rooney finally created a half chance on the edge of the box for the visitors on 19 minutes when he made a yard of space but fired wide with his left foot.

United were rocking again on 34 minutes, though, after a sloppy pass from Jonny Evans allowed Massimo Ambrosini to play in Klaas-Jan Huntelaar but his rasping low drive fizzed just wide.

And then, out of nothing United were level on 36 minutes.

If Milan's opener owed something to luck, United's equaliser was no more lacking in that department.

Darren Fletcher crossed from the right for Scholes arriving in the box but he missed with his swinging right foot and the ball hit his standing left leg, spun beyond Dida and trickled in off the post.

Milan almost caught United napping again three minutes into the second period as Pato stole in unchecked onto Giuseppe Favalli's deep cross but the young Brazilian headed over.

United started to get a foothold in the game with Rooney coming to the fore, seeing one shot deflected for a corner and hitting a volley wide before Van der Sar had to tip away a curling Ronaldinho effort.

Nani was having one of his more erratic days and Ferguson replaced him with Anotnio Valencia halfway through the second period, a move that bore fruit within a minute as the Ecuador flyer got to the byline and crossed for Rooney at the back post to flick a floating header over Dida for his 25th goal of the season.

United were now content to hit Milan on the counter and Rooney flashed a shot just wide on 73 minutes but a minute later he ran onto Fletcher's dink into the box past a static defence to head easily past Dida.

United were cruising until a late lapse allowed in Seedorf, who had replaced Beckham, to lift the crowd and give the visitors a nervous last few minutes.