Result: Ten-man AC Milan seal last-16 spot

Milan produce a herculean effort to book their place in the last-16 of the Champions League at expense of Ajax, despite playing with 10 men for most of the contest.

Ten-man AC Milan held off the challenge of Ajax to book their place in the last-16 stage of the Champions League tonight.

AC Milan's midfielder Riccardo Montolivo fights for the ball with Ajax's midfielder Davy Klaassen during the group H Champions League football match AC Milan vs Ajax, on December 11, 2013© Getty Images

The Rossoneri, who needed only a point from their Dutch counterparts to book their place in the second round of the competition, faced an uphill task in their bid to seal progression.

Riccardo Montolivo's 22nd-minute red card handed the Dutch a numerical advantage in their quest to reach the latter stages but ultimately Massimiliano Allegri's men held on.

Frank de Boer's men, who needed all three points to progress at the expense of Milan, came within the width of the post from taking a fifth-minute lead.

Christian Poulsen rose highest from a Lasse Schone corner but the Dane saw his header cannon off the post.

The visitors came close again on 21 minutes, as Davey Klaassen saw his diving header well saved by goalkeeper Christian Abbiati.

Montolivo was soon dismissed for a late challenge on Poulsen to give Allegri's charges a testing second half.

Despite their numerical advantage, The Amsterdam-based outfit failed in their bid to overcome the resolute Italians and the hosts held on to secure their progression.

AC Milan's midfielder Riccardo Montolivo fights for the ball with Ajax's midfielder Davy Klaassen during the group H Champions League football match AC Milan vs Ajax, on December 11, 2013
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