Montolivo was shown a straight red by referee Howard Webb after just 21 minutes but despite intense pressure from the Dutch champions Milan held on to record a crucial 0-0 draw, relieving the pressure on manager Max Allegri.
Ajax came within an inch of breaking the deadlock after just eight minutes, when Christian Poulsen’s glancing header from an out-swinging corner kick flashed across the face of goal and bounced off the inside of the Milan post and into Christian Abbiati’s arms.
Milan were reduced to ten men after just 21 minutes, when Montolivo was shown a straight red card for a late and reckless challenge on Poulsen, stamping on the midfielder’s ankle with dangerous force.
Frank De Boer threw on Danny Hoesen at the break to give his side more threat going forward but Milan repelled their every attack, with Abbiati making a solid stop from Davy Klaasen after the hour mark.
Viktor Fischer flashed a low shot just past the post with less than 20 minutes remaining, before Klaasen came close to breaking Milan hearts with the last kick of the ball, sending an improvised overhead kick towards goal. However, the ball flew inches past the post while the San Siro held its breath.
8’ - WOODWORK: Ajax come close to opening the scoring, when Christian Poulsen’s glancing header bounced off the inside of Christian Abbiati’s left hand post.
21’ - RED CARD: The home side were reduced to ten men when Riccardo Montolivo was shown a straight red for a reckless, stamped challenge on Christian Poulsen.
67’ - SHOULD DO BETTER: Abbiati pulled off a good save to deny Davy Klaasen after a good passing move across the edge of the box by Ajax. Should have done better though.
95’ - LAST OPPORTUNITY: Klaasen almost bagged a dramatic winner with the last kick of the game, sending an improvised overhead kick from inside the box just past the target.
AC Milan have now qualified for the last 16 of the Champions League for the 11th consecutive time.
By keeping a clean sheet AC Milan have conceded just one goal in their last four home games in the Champions League.
Ajax enjoyed 71% of the possession, recording 25 attempts on goal compared to just four by AC Milan.
TALKING POINT – Can AC Milan carry the flag for Italy? While Milan were edging their way into the last 16 Napoli were pushed out thanks to a late Borussia Dortmund goal in Marseille. And Juventus’ defeat at Galatasaray earlier means Milan are the only Italian side left in the Champions League. League form would suggest they have no hope of mounting a genuine challenge, but Allegri’s side always seem to up their game in Europe.
MAN OF THE MATCH
Mattia De Sciglio, Milan - The young left back strengthened his already burgeoning reputation as one of Italy’s brightest young prospects, digging out his fellow defenders and even his keeper on a number of occasions. In the rare event of a Milan attack he also provided an effective outlet down the wing.
AC Milan: Abbiati 6, De Sciglio 8, Bonera 7, Zapata 7, Constant 6, De Jong 6, Montolivo 2, Muntari 7, Kaka 7, El Shaarawy 4, Balotelli 5. Subs: Poli 6.
Ajax: Cillessen 5, Van Rhjn 6, Moisander 5, Denswil 5, Blind 7, Poulsen 6, Klaasen 7, Serero 6, Schone 6, Fischer 7, Bojan 4. Subs: Hoesen 6, Sigthorsson 5.
MATCH IN A TWEET