Champions League: Round of 16 AC Milan 2-3 Manchester United Leg One

Peter LomuscioCorrespondent IFebruary 17, 2010

MILAN, ITALY - FEBRUARY 16: Darren Fletcher (R) of Manchester United celebrates with team mate Wayne Rooney after Rooney scored their third goal during the UEFA Champions League round of 16 first leg match between AC Milan and Manchester United at Stadio Giuseppe Meazza on February 16, 2010 in Milan, Italy.  (Photo by Hamish Blair/Getty Images)
Hamish Blair/Getty Images

The Stadio Giuseppe Meazza was the site for the much-anticipated first leg of the UEFA Champions League Round of 16 clash between AC Milan and Manchester United.

AC Milan manager Leonardo was faced with multiple decisions heading into this match when formulating his starting 11. Key contributors, striker Marco Borriello and rightback Gianluca Zambrotta, were both out due to injuries. This opened the opportunity for last weekend’s hero Klaas Jan Huntelaar to get the start at striker with the Brazilian duo of Ronaldinhoo and the now healthy Pato in support of him.

In the midfield, the Rossoneri went with the reliable and productive pair of Massimo Ambrosini and Andrea Pirlo—no surprises there. The third midfielder selection went to the former Red Devil David Beckham. Beckham got the manager’s nod in place of the feisty Italian Gennaro Gattuso, who was pushed to the bench for the start of this one. The four in the back were Luca Antonini, Thiago Silva, Alessandro Nesta and Daniele Bonera.

Leonardo went with the experience selecting Bonera over the speedy young Abate. The goalkeeper was the shaky Brazilian Dida.

Manchester United manager Sir Alex Ferguson also had some last-minute decisions before the big first leg. Absent from the roster were backs John O’Shea and Nemanja Vidic and midfielders Anderson and the recently injured Ryan Giggs. Rio Ferdinand was able to suit up and take his normal spot in anchoring the central defense.

Partnering up with Ferdinand in the central defense was Jonny Evans, and the outside backs were Evra and Rafael. The trio in the central midfield was Paul Scholes, Darren Fletcher and Michael Carrick. On the wings, Ferguson went with Nani and the full of energy Ji-Sung Park. Wayne Rooney was the man upfront and clearly the focus of all AC Milan defenders.

The sellout crowd of 80,000 fans was buzzing at the kickoff, and it didn’t take long before the Italian fans at the San Siro were given reason to celebrate.

In the third minute a David Beckham free kick was sent spinning into the area, where Patrice Evra botched an attempted clearance, sending the ball across the area right to the foot of Ronaldinho. He promptly volleyed the ball off Michael Carrick, leaving the keeper no chance and giving Milan the 1-0 lead. Van der Sar was sprawling to one side of the net only for the deflection to send the shot elsewhere. Pato won the free kick after being cut down by Evra.

AC Milan looked to continue their attack in the seventh minute, when Ronaldinho created space in the box around his defender, only to release a shot easily within the keepers reach.

The 11th minute arose another glorious chance for the Rossoneri when Thiago Silva was able to basically walk right through the defensive midfield of Manchester United sending in leftback Luca Antonini. He cut inside his defender only to drag his shot just wide of the near post.

A minute later, Manchester United won a corner after a neatly done give and go between Nani and Park. On the corner, Milan keeper Nelson Dida was back to his clumsy ways, spilling an easy gather and sending Milan supporters into panic before he recovered to collect the ball.

Ronaldinho found himself applying another dangerous threat to United after he collected a sloppy giveaway, only to walk in one-on-one with Manchester captain Rio Ferdinand. After a series of scissor moves, Ronaldinho was clipped on the ankle just at the top of the area. The referee waived play on, as he clearly missed the contact.

Ferdinand was extremely fortunate because it obviously would have been as dangerous of a free kick spot as there is and was clearly a bookable offense on top of that.

The 19th minute gave the Red Devils their first legitimate scoring chance when Wayne Rooney lashed a strong left footed shot just wide of Dida and the net.

A five-minute spell came upon United once the 29th minute rolled along. A careless turnover in their own end lead to a dangerous Pato running towards their area, but nothing came of it after Huntelaar ran himself and his defender into all of the available attacking space the young Brazilian had.

In the 32nd minute, another careless giveaway by United’s Evans led to a dangerous Huntelaar rip that Evra was able to get his body in the way of to deflect it wide. The 34th minute brought along a further Manchester mistake that Ambrosini gathered and simply sent Huntelaar through the center of United’s defense, but his sliding attempt once again missed the target in what was clearly his most glorious scoring attempt of the night.

After surviving the mistakes and Milan threats, Manchester got a chance of its own. Milan leftback Luca Antonini got banged up, and when he went down, it sent the Milan defense and midfield into a brief scramble. The ball-chasing defense gave United just the room they needed to free Fletcher along the right wing to send in a cross.

Paul Scholes ran onto the cross and swung an attempt at the ball only to whiff at it, but as he missed with his right leg, the ball connected on the shin of his plant leg sending the ball spinning to the far post where it rolled in to tie the match 1-1.

Ronaldinho did his best to respond just minutes later when he maneuvered himself through two United defenders to send a fierce shot, stinging the hands of Van der Sar. The keeper did a fantastic job stopping this sharp bouncing effort on goal.

On the final play of the half, Thiago Silva sent a dangerous ball across the area towards the far post, but it was all spectators as no one made a move towards the pass and it bounced across the end line untouched.

The second half got underway, and Manchester United looked to be the hungrier side from the get go. Nani was able to loft a hazardous cross to the far post in the 47th minute where a leaping Fletcher just headed wide almost catching a lackadaisical Milan defense snoozing.

Milan regrouped and was able to create a few stray chances of their own. One being in the 48th minute when Favalli lashed a left-footed cross into the penalty spot, where Pato met the pass with a sharp threatening header just off target.

In the 52nd minute, Pirlo struck a superb free kick from 35 yards out, but Van der Sar was able to tip it over the bar. In the 60th minute, Pato did well to create space for Ronaldinho, who side footed a shot on goal that was routinely handled by Van der Sar.

Manchester United’s breakthrough came in the 66th minute. Fresh off the bench Valencia was able to send in a precise cross to a leaping Rooney at the far post, where he headed across the goal smoothly to easily beat the keeper. This goal deflated the home side giving United the 2-1 lead.

Minutes later the space continued to grow for the momentum filled Red Devils. In the 73rd minute, Rooney put the space to use when he buzzed another effort just wide.

A minute after the Milan defense was once again exposed badly, they paid the ultimate price. A free-roaming Rooney ran onto a precise chipped pass from Fletcher to head in another to give Man U the commanding 3-1 lead.

Just when it seemed all the hope was gone for the Rossoneri, they hit on an 85th minute goal when the substitute, Seedorf, cleverly healed in a perfect pass from Ronaldinho to cut the lead to 3-2.

Seconds later, Ronaldinho almost set up another goal for yet another substitute. This time it was Flippo Inzaghi. The Brazilian lead Inzaghi precisely, only for the striker to scorch his shot inches off the target as Van der Sar stood helpless.

With the final whistle approaching, AC Milan gave their best effort to apply some serious pressure in search of the equalizer. The crowd was back to life and in full force. Ambrosini collected possession of a knocked down ball in the area. Just as he created space to rip a close range shot from about eight yards out, a desperate sprawling block from the Manchester captain Rio Ferdinand deflected the shot wide.

On the corner kick, Thiago Silva jumped in front of Nesta, only to head over the target and end Milan’s search for the equalizing goal.

In stoppage time, Manchester United was dealt a negative blow, though when Michael Carrick received his second yellow card of the match after an unnecessary time-wasting stunt. It was definitely rather harsh for the United midfielder, but it was wrong place wrong time for the lad. The referee was bound to punish one of the Manchester United players after numerous time-wasting occurrences.

So at the final whistle, Manchester United not only were victorious at the San Siro, but they tallied three crucial away goals in a 3-2 win. The Red Devils outlasted the Rossoneri behind the overall squad stamina and the finishing of Wayne Rooney. Darren Fletcher and Valencia were the key contributors in the second half counter attacks, and the defense did just enough to survive in the final minutes to preserve the result.

AC Milan failed miserably to convert on so many splendid scoring opportunities, and this cost them dearly. In what could have been a memorable night for the Italian side turned into a disastrous one. Milan lacked bite in the midfield and ran out of gas in the second half. They were never organized in the back, and the age and lack of hustle paid its toll in the second half.

All that being said Milan still had way more scoring chances and can easily be labeled unfortunate for this harsh result.

Looking forward to the second leg at Old Trafford, Manchester United is clearly feeling comfortable in the drivers seat. They will be content to draw despite all the attack talk they will probably spew to the public. The Rossoneri, on the other hand, will have to travel well in the second leg and play one of the matches of their season if they plan to overcome this one.

One thing is for certain, Milan will need to bring their goal-scoring boots.

Player Ratings


AC Milan

Dida—4.5 Wasn’t at fault for any of the three goals, but still was clumsy to say the least. Clearly shouldn’t be Milan’s starting goalkeeper, but what options are there?

Antonini—6.5 Before getting injured and subbed off in the 38th minute he was very productive. Was running with Nani well and also managed to provide a great scoring opportunity early on with a nice run up the wing. Did well covering for Ronaldhino.

Thiago Silva—5.0 The Brazilian back did well in his trips up the pitch, especially when he set up Antonini on the wing early on. But lazily let Rooney run away from him into the area freely for the dagger and third goal for United. Also missed late header that could have tied it.

Nesta—5.0 The central defender didn’t have one of his best days. Botched Clearances early on, along with unexpected poor marking and being beaten to the ball on multiple commits. Did settle down in second half, but by then the rest of his teammates didn’t have an ounce of defense left in them.

Bonera—6.0 Was at his best in the first half of play. Confident on the ball and prevented any attacks from his portion of the pitch. The second half was a different story though. Clearly ran out of gas and just looked out of place. Was out jumped by Rooney for United’s second goal.


Ambrosini—6.0 Solid performance from the captain. Was key in the defensive role all night. Covered for Pato and Ronaldinho all match. Created Huntelaar’s best scoring opportunity. Will be agonizing over his missed late scoring chance for weeks to come.

Pirlo—5.5 Nothing extraordinary from the Italian playmaker tonight missed Gattuso’s enforcing play in the midfield.


Beckham—5.0 Didn’t stand out against his former side tonight. Probably shouldn’t have started in hindsight. His free kick led to the goal, but he cant be given credit for that.

Ronaldinho—7.5  The flashy Brazilian looked as if he brought out all the tricks tonight. From the backheels, to the flicks, to the magical playmaking ability. His volley put Milan in front and his assist provided some very minuscule hope for the rest of the match and the second leg.

Would definitely have a higher rating if it wasn’t for his complete absence of any defense or hustle to win back lost possessions. But he created too many scoring chances to receive anything lower of a rating.

Pato—5.0 Just couldn’t get it going tonight. Didn’t have his best dribbling skills on him and clearly lacks chemistry with Huntelaar.

Huntelaar—4.5 The Dutchman is sure to be full of disappointment after this contest. Missed a handful of scoring chances and can easily be labeled the goat of the match.




Favalli—4.5 Came on for Antonini in the 38th minute and tried his best to put on a serviceable performance. His lack of pace was clearly a factor, as the cushion he provided Manchester attacks proved vital.

Seedorf—6.5 The veteran Dutchman came on in the 72nd minute and looked rusty and slow off the bat. But he quickly erased the criticisms after a creative finish on Milan’s second goal.

Inzaghi—5.0 Came on in the 77th minute and missed his one scoring opportunity.



Manchester United


Van der Sar—6.0 The Dutch keeper wasn’t at fault for either of the two goals and made multiple key saves.

Evra—6.0 The French back started off sloppily, as Pato seemed to get the best of him early on, but recovered to cancel out the Brazilian for the remainder of the match.

Evans—4.5 Nerves clearly got to this young defenseman, as he was at fault for numerous inexcusable giveaways in his own end. Poor defending all night and was not prepared for the big stage.

Ferdinand—6.0 The captain was solid overall. Kept Huntelaar off the mark and blocked what was clearly about to be the equalizing goal from the foot of Ambrosini at the death.

Rafael—5.0 Was beaten and taken to the cleaners by an in form Ronaldinho for the majority of the match. 

Fletcher—7.0 Was composed and patient in the midfield all match. Assisted on Scholes opener and Rooney’s second goal with splendid crosses. Was key to United’s link up on their counter attacks.


Carrick—5.5 Patrolled the midfield and held his position respectfully. Was sent off in stoppage time after receiving his second yellow card for a foolish time wasting maneuver. Was extremely unfortunate for the lad. Wrong place wrong time. Not worthy of a red card and a suspension.


Scholes—6.5 Scored United’s first goal with luck on his side, but there was nothing lucky about his strong midfield play where he effectively produced all match.

Park—5.0 Ran the pitch as usual, but didn’t play a big role in the match as he was barely seen or mentioned.

Nani—5.5 Provided a threat on the wing with the ball on his feet, but failed to produce to his ability. Didn’t look to be fit and was subbed out in the 65th minute.


Rooney—8.0 Scored twice on headers that he made seem effortless. Great finishing by the Englishman. Provided a treacherous threat every time he had possession near the area.


Valencia—7.0 Brought on in the 65th minute and produced immediately with a precise cross to set up Rooney’s first goal. Was a threat on the wing almost every time he touched ball with the mismatch he provided on the outside.


Man of the Match: Wayne Rooney, Manchester United

Referee—Olegario Benquerenca (Port)—5.0


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