Milan - Inter Milan crashed out of the Champions League on Tuesday after being held 1-1 by PSV Eindhoven at the San Siro thanks to Group B rivals Tottenham Hotspur gaining a point against Barcelona.
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The Serie A side needed to better Spurs' result at the Camp Nou in order to overtake the Premier League outfit and snatch a place in the knock out rounds.
Luciano Spalletti's side thought they had done enough in the 73rd minute when captain Mauro Icardi marked his 200th game for the club by equalising Hirving Lozano's 13th-minute opener, with Spurs a goal down in Catalonia.
However Lucas Moura levelled at 1-1 for Tottenham, enabling his team to advance to the last 16 thanks to the away goal they scored in their 2-1 defeat at the San Siro.
Inter lost 1-0 at Tottenham last time out, meaning Spurs go through in second place with a superior head-to-head record.
The hosts had gotten off to a good start against already eliminated PSV, coached former AC Milan midfielder Mark van Bommel.
Icardi sent in a long ball five minutes into the game which Ivan Persic got his head to but the Croat's effort clipped the post.
After the initial scare PSV regrouped their defence and proved increasingly dangerous on the counterattack.
The Dutch broke through following a monstrous blunder by Inter midfielder Kwadwo Asamoah.
The Ghanian was caught in possession by Steven Bergwijn, with the ball flying across the face of goal and Lozano nodding in at the back post.
Asamoah struggled throughout the first half and almost conceded a second with an accidental assist for Luuk De Jong, but Samir Handanovic rushed off his line to parry.
Icardi fired a chance wide before the break before Handanovic tipped a Bergwijn effort over the bar.
The Dutch could thank goalkeeper Jeroen Zoet after the break when he denied Icardi, Stefan De Vrij and Keita Balde.
But Icardi blasted in the equaliser midway through the second half, picking up a perfect cross from Matteo Politano which left Zoet with no chance.
The Italians piled forward in search of the winner but could not break through, with substitute Lautaro Martinez sending a header over the bar late-on.
The Dutch club, who won the European Cup in 1988, achieved just their second point of the competition as they finished bottom of the group behind Inter.