Clarence Seedorf's coaching debut in the UEFA Champions League ended in defeat as Milan were beaten 1-0 by Atletico Madrid on Wednesday.
Milan looked on course for a well-deserved draw after having the better chances in the match, however Diego Costa struck his fifth goal in four Champions League games in the 83rd minute to win the round-of-16 first-leg clash.
The Serie A side had the better of the first half with excellent opportunities to open the scoring, but they lacked quality in front of goal as Andrea Poli and Kaka both missed good chances, while visiting goalkeeper Thibaut Courtois was in inspired form.
Atleti improved after the interval, but chances for either side were few and far between, with Christian Abbiati only called into action once in the whole game by the visitors until Costa powered a header beyond him in the closing stages.
The result gives Atleti a crucial away goal going into the second leg at the Vicente Calderon in three weeks' time.
Diego Simeone's side attacked from the off, though Abbiati was untested and Milan slowly worked their way back into the game with good spells of possession.
They created a number of good opportunities to break the deadlock but suffered from a lack of accuracy in their finishing, and found Courtois in fine form when they did get the ball on target.
The Belgian goalkeeper diverted Kaka’s effort onto the crossbar in the 15th minute, and three minutes later he produced an outstanding stop to tip Poli’s close-range header onto the post.
Kaka went close again for the hosts after latching onto a backheel from Mario Balotelli, but the Brazilian curled his effort just over the bar.
Clarence Seedorf will have been impressed with his side's performance but they failed to capitalise, Balotelli missing the last chance of the first half as his long-range effort bent wide of goal.
With the words of Simeone no doubt ringing in their ears, Atleti came out for the second half with renewed energy, but clear-cut chances were still not forthcoming.
After a quiet opening period, Costa saw an attempted acrobatic volley fly way over the bar and an effort from Raul Garcia went the same way with the midfielder's low effort smothered by Abbiati as chances of a goal looked to be running out.
However, with seven minutes to play, the veteran goalkeeper was unable to get anywhere near a header from Costa, the Brazilian pulling away from his marker to give the visitors victory.
Adil Rami went close to levelling for Milan with a powerful long-range effort but it flew wide of Courtois' right-hand post and Milan have it all to in Spain on March 11, having won on just one of their last 13 trips to La Liga sides.
|2||M. De Sciglio|
|34||N. de Jong|
|Coach: C. Seedorf|
for M. De Sciglio 26'
for M. Balotelli 78'
for A. Poli 85'
|Klose lauds Ronaldo after scooping record|
|Iran refute Susic claims|
|Fernandez named Deportivo boss|
|Argentina have no chance, says Robben|
|Hierro to replace Zidane as Real first-team coach|
|Rhodes signs new Rovers deal|
|Arsenal complete Sanchez swoop|
|Inzaghi backs under-fire Balotelli|
|Defeat has overshadowed display - Vlaar|
|Maradona: Germany full of themselves|
|Barry hoping for England recall|
|Green extends QPR stay|
|Shanghai Shenhua 1 Guangzhou Evergrande 2: Rong leaves it late in dramatic win|
|Germany hope for Brazilian support|
|Torino striker Cerci in demand|
|FIFA critcised following Mascherano incident|
|Bernat happy at Bayern despite bad memories|
|Giggs backs Van Gaal to thrive at Old Trafford|
|Tadic can fill Lallana void - Koeman|
|New five-year deal for Nasri|
|Barcelona release injury-hit Cuenca|
|Suarez appeal rejected|
|La Decima a reflection of Di Stefano - Perez|
|Buoyant Mazzarri eager for Inter success|
|Mandzukic joins Atletico|
|Van Gaal criticises third-place play-off|
|Halilhodzic yet to decide future|
|Mandzukic eager for Simeone link-up|
|Davies hoping for Hull deal|
|Poyet hopeful over Altidore fitness|
|Diego close to ´dream´ Fenerbahce move|
|Inter loan out youngsters|
|Fired-up Cole can inspire Villa, claims Lambert|
|Hughes hailed for winning over Brit doubters|
|Hajrovic signs for Bremen|
|Hull can buck Europa League trend, says Meyler|
|Mertesacker talks up German chances|
|Swansea reveal Tottenham contact over Davies, Sigurdsson|
|Lloris pens five-year deal at Tottenham|
|Fernandinho: ´The pain is big´|
|MLS Preview: Portland aim for swift revenge against Seattle|
|Sabella: Germany have an advantage|
|Second Argentine journalist dies in Brazil|
|Aguero: Argentina defied critics|
|Impressive Mascherano thrilled with final´s berth|
|Zuniga offered protection by Colombia|
|Germany vowed not to ´humiliate´ Brazil|
|Hong resigns from South Korea post|
|Third-choice Vlaar ´wasn´t nervous´|
|Van Gaal: I wanted Krul in the shootout|
|Argentina: Key factors in reaching the final|
|Sabella revels in semi-final win|
|Proud Robben feels pain of World Cup exit|
|FIFA World Cup: Netherlands 0 Argentina 0 (after extra time, 2-4 on penalties)|
|Susic signs two-year extension with Bosnia-Herzegovina|
|Hummels in race to make World Cup final|
|Scolari still baffled by Brazil collapse|
|Spendlhofer and Benedetti leave Inter|
|Neymar ´recovering well´ from injury|
|Villarreal sign Jonathan dos Santos|
|Arteta happy at Arsenal, insists agent|
|Birsa makes Chievo loan switch|
|FIFA suspends Nigeria over political interference|
|Di Stefano funeral held in Madrid|
|Hangeland scathing of ´difficult´ Magath|
|Thiago Silva in fan plea|
|Isgrove earns fresh one-year deal at Southampton|
|Morata edges closer to Juve switch|
|Nugent pens two-year extension at Leicester|
|Gomez delight with ´perfect´ Germany|
|Costa Rica to discuss Pinto future|
|Arfield agrees Burnley extension|
|Allardyce targets four more signings|
|K.League Review: Jeonnam close gap on Pohang, Jeonbuk|
|Maradona: Thrashing damages Brazil´s image|
|Kasami makes Olympiacos move|
|Chelsea complete Pasalic signing|
|Helenius makes temporary Aalborg return|
|Higuain set for Napoli stay|
|Basta targets return to Europe with Lazio|
|Lewandowski willing to adapt for Bayern|
|New Hull deal for Jakupovic|
|Atletico agree Mandzukic deal, claims Sammer|
|Fulham seal Stafylidis loan|
|Alves pens new Valencia deal|
|Ochoa to take time over future|
|Brown could miss three months|
|Adams: Norwich will not overspend|
|Gundogan unsure when rehab can step up|
|Stoke chairman wants long Begovic stay|
|Brazilian media reacts to semi-final exit|
|Icardi vows to remain at Inter|
|Robben is player of the World Cup, says Kluivert|
|Klose focused on final after breaking record|
|Prandelli takes aim at Balotelli, Rossi|
|Schweinsteiger sorry for Brazil battering|
|Brazil scarred for life, says Fred|
|Sabella: Argentina ´have already won´|
|Muller stunned by rout|
|Low lauds ice-cool Germany|
|Tearful Luiz apologizes for semi-final loss|
|Scolari sorry for ´catastrophic´ Brazil hammering|
|Brazil join sport´s biggest chokers|
|Reality kills Brazilian dream on a surreal night|
|FIFA World Cup: Brazil 1 Germany 7|