MILAN - Ten-man AC Milan resisted a spirited Ajax to hold the Dutch giants to a goalless draw and book their place in the last 16 of the Champions League on Wednesday.
Seven-time champions Milan welcomed Frank De Boer's men to the San Siro stadium confident of claiming the point that would seal their entry to the knockout phase.
But after an auspicious start the Rossoneri's hopes suffered a huge blow when captain Riccardo Montolivo saw red in the 19th minute for a late tackle on midfielder Christian Poulsen.
Ajax shaded a fairly balanced first half and were unlucky not to have scored in the fifth minute when the woodwork saved Milan 'keeper Christian Abbiati after he had been beaten by Poulsen's header.
Yet despite Ajax enjoying most of the possession in a dominant second half and laying siege to the Milan goal in the last quarter hour, Massimiliano Allegri's men held firm to finish second in Group H behind Barcelona.
"The team really deserve this qualification. Against Ajax it was always going to be complicated, but it became even moreso after we were reduced to 10 men," said Allegri.
Ajax coach Frank De Boer said his side, held to a 1-1 draw by Milan in Amsterdam, did not deserve to exit the competition.
"Looking at the two matches, I would say we deserved more than to finish in third place," said De Boer, whose side drop into the Europa League.
Milan's only real chance of the opening half came in the fourth minute when striker Mario Balotelli tested Jasper Cillessen with a dipping free kick which the keeper got down low to collect.
Just a minute later Poulsen was unlucky to see his header from a corner sail over the Milan defence only to come off Abbiati's far post.