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'
|Griezmann must think before he speaks - Saul|
|Rooney: I decided to take corners instead of Kane at Euros|
|Benteke: My time at Liverpool was not a failure|
|Asensio: I had the chance to join Barca|
|Morata: I had five or six phone calls every day|
|Costa: I wanted to return to Atletico|
|Mascherano: It would have been ´a sin´ for Messi to stay in international retirement|
|Guardiola: No one plays better than Barcelona|
|Sigthorsson seals Galatasaray loan move|
|Griezmann urges France to forget Euro 2016|
|Konoplyanka joins Schalke on loan|
|Mustafi finalises Arsenal move|
|Chambers loaned to Middlesbrough by Arsenal|
|Ajax snap up Ziyech from Twente|
|Kenedy joins Watford on loan from Chelsea|
|Cuca backs ´golden boy´ Gabriel Jesus to take off at Man City|
|Aguero´s brother joins Cadiz on loan|
|Leicester made €30m bid for Adrien Silva, father reveals|
|Schweinsteiger feels ´deep gratitude´ for Germany career|
|Swansea complete deal for Barnsley defender Mawson|
|Perez delight at Arsenal signing|
|Inter complete Gabriel capture|
|Mariappa returns to Watford|
|Aguero charged over Reid elbow|
|Hart pictured with Torino shirt ahead of loan switch|
|Albrighton pens fresh Leicester deal|
|Hull seal club-record Mason swoop|
|Pjanic confident Juve debut is on the horizon|
|Lucescu confirms Juventus interest in Witsel after Everton snub|
|Messi trains ahead of Argentina return|
|Villa sign Kodjia in a deal worth up to £15m|
|Marshall leaves Cardiff and heads to Hull|
|Rosicky returns to Sparta Prague|
|Gnabry close to Werder Bremen switch|
|Arsenal complete Perez deal|
|Celtic sign Gamboa from West Brom|
|Remy joins Palace on season-long loan|
|Kante like a rat - Hazard|
|Rooney proud to break England outfield caps record|
|Rooney to quit international football after World Cup|
|Barcelona sign €30m Valencia striker Alcacer|
|Koke and Vazquez welcome Laporte to Spain fold|
|Schweinsteiger has no ´personal problems´ with Mourinho|
|Alcacer, Hart, Wilshere and the deadline-beating deals still to come|
|Antonio thought first England call-up was banter|
|Premier League a completely different market - Heidel|
|Lens completes Fenerbahce loan move|
|Pescara awarded points after Sassuolo field ineligible player|
|Lyon calm Lacazette injury fears|
|Bamford joins Burnley on loan|
|Van Basten to leave Netherlands´ backroom staff for FIFA role|
|Ventura perfect for Italy - Verratti|
|Martial needs to be more consistent - Deschamps|
|Verratti not happy at PSG - Ventura|
|Ventura: I´ll probably manage Chelsea when Conte leaves|
|Bartomeu: Barca discussing new contract with Messi|
|Bauza: No doubts over Messi motivation|
|Schmeichel targets quick return after surgery|
|Giovinco to help aid earthquake victims in Italy|
|Ancelotti backs Madrid for LaLiga and Ronaldo to be top goalscorer|
|Gomes: Portugal can deal with Ronaldo absence|
|Sterling reveals Guardiola impact|
|Fiorentina deny approach for Chelsea target Alonso|
|Allardyce confirms Rooney retains England captaincy|
|Hart to join Torino – agent|
|Sanches withdrawn from Portugal squad|
|Sporting CP issue Adrien Silva clarification amid Leicester links|
|Watford confirm Okaka signing|
|Manchester City outcast Zuculini seals Rayo Vallecano loan switch|
|Dembele offers something different - Deschamps|
|Sunderland would just love to get rid of me - Lens|
|No Casillas in Spain squad represents a ´new era´, says Ramos|
|Zenit defender Criscito could return to Italy, claims agent|
|Barcelona reveal Messi hamstring injury|
|Modric named new Croatia captain|
|Napoli announce Rog signing|
|De Boer is building something at Inter - Morratti|
|Keane eyes coaching career after international retirement|
|Bravo left out of Chile squad for family reasons|
|West Brom announce Chadli signing|
|Former Dodgers owner set for Marseille purchase|
|Ferdinand: I reached out to Wenger|
|Holgate has big quality for a young player - Koeman|
|Manchester United want to keep Rojo, says agent|
|Low not concerned by captaincy as Germany bid farewell to greats|
|Aguero pulls out of Argentina squad|
|Howedes: Germany must prove themselves all over again|
|Ventura close to tears on first day of Italy training|
|Torino interested in City outcast Hart|
|Adrien Silva hoping to seal ´exceptional´ Leicester switch|
|Boufal joins Southampton from Lille for club-record fee|
|Villa outcast Lescott joins AEK Athens|
|Milner: I´m learning left-back role as fast as I can|
|Allardyce ready for Hart transfer disruption|
|´Door always open´ for Barkley - Allardyce|
|Xhaka like Petit, claims Wenger|
|Coric: I was a medical away from joining Liverpool|
|Pasalic keen to put injury troubles behind him at Milan|
|Guardiola delighted with Sterling form|
|Rooney should retire from England duty - Shearer|
|Hazard can ´decide´ the title - Ivanovic|
|Allardyce hails ´outstanding´ Antonio|
|Belgium can make history - Henry|
|Nice president: Call Balotelli and tell him we need a striker|
|Modric would like to see out career in Madrid|
|Geromel replaces Caio in Brazil squad|
|Mustafi: Ozil convinced me to join Arsenal|
|Pardew confirms ´one or two´ more signings|
|MLS Review: Kaka brace denies NYC top spot, Timbers beat Sounders|
|Mihajlovic: I won´t waste anymore breath on Maksimovic|
|Okon named Central Coast Mariners coach|
|´Special´ Rashford will get chance - Rooney|
|Injury forces Schurrle out of Germany squad|
|Burke snubs Premier League interest to join RB Leipzig|
|Guardiola: Nasri has a future at City, if he wants it|
|Klopp confident ´all will be good´ with Sturridge|
|Emery confident PSG will bounce back|
|Athletic may strengthen squad - Valverde|