When Portsmouth beat Cardiff City to win the FA Cup in 2008, their success ensured that they qualified for the UEFA Cup for the first time in their history, creating the possibility of fixtures that were once considered only achievable on computer games FIFA or Pro Evolution Soccer. However, after edging past Portuguese club Vitoria Guimaraes in the first round, Pompey found themselves included in the 40-team draw for the group stages and in with a realistic chance of being handed a number of glamour ties.
With Portsmouth being in the fourth seeding pot of five, they would inevitably be up against it to progress further in the competition, but that mattered little to the South Coast side after they were drawn alongside AC Milan, the seven-time European champions, as well as Wolfsburg, Braga and Heerenveen. There was excitement for each individual match, but nothing like the anticipation ahead of their home match with Milan, who would make the trip to Fratton Park on this day seven years ago.
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After being heavily beaten to Braga in their opening match, Portsmouth were aware that they needed a positive result against the Italian giants in order to maintain genuine hope of reaching the knockout stages. As for Milan, a squad featuring the likes of Kaka, Ronaldinho, Andriy Shevchenko and Filippo Inzaghi had already recorded two victories and only required another point to guarantee a spot in the top three of the table.
Portsmouth went into the fixture on the back of a three-game unbeaten run in the Premier League under the guidance of Tony Adams, who was taking charge of his first European fixture. It was a big ask of the former Arsenal skipper, who had only previously managed Wycombe Wanderers, but his team started confidently against their high-profile opponents before suffering a scare in the 11th minute when Inzaghi struck the ball against the post.
Shevchenko also wasted a chance inside the penalty area before Inzaghi chipped the ball against the top of the crossbar. Portsmouth had their moments in the opening 45 minutes, too, with Peter Crouch and Nwankwo Kanu proving a constant threat to Philippe Senderos, who was struggling to deal with high balls floated into the box by full-backs Glen Johnson and Nacer Belhadj. There was a feeling of pride and relief as Portsmouth reached the break on level terms, but what would transpire in the second half would leave everyone associated with the club with mixed feelings come full time.
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After keeping Milan out for over an hour, Portsmouth took the lead on 62 minutes when Younes Kaboul got above Senderos to power a header into the bottom corner after being found by Johnson from the right flank. The former Chelsea full-back was full of confidence after scoring what turned out to be the goal of the month for November against Hull during the previous weekend, and that extra belief paid off further just 11 minutes later as he danced past two Milan defenders before providing Kanu with the simplest of tasks from three yards out.
However, despite the game entering the final 10 minutes, there was never the feeling that Portsmouth were safe, and with six minutes left, everyone was reminded why. In trademark fashion, Ronaldinho stepped up to curl a free kick into the top corner from 25 yards out to score a goal which created panic and indecision in the home team's backline for the remainder of the match, something which hurt them in the second minute of added-on time.
After the ball was volleyed into the penalty area, Inzaghi brought it down with the deftest of touches, which wrong-footed two Portsmouth defenders in the process, before he poked the ball into the corner from no more than six yards to deny Pompey what would have undoubtedly been the most famous triumph in their history. It was also a goal that saw Milan progress through to the knockout stages and left their English opponents with too much to do in their final two group fixtures.
Milan boss Carlo Ancelotti admitted after the match that his side were "a bit lucky", while Adams said that his squad were "really flat and upset" after failing to hang on until the end. The contrasting emotions summed up what was an unforgettable night in the history of a club who now ply their trade in the fourth tier of English football - they just didn't expect to be feeling disappointment having earned a point against one of the biggest clubs in world football.
Portsmouth: James, Johnson, Kaboul, Distin, Belhadj, Little (Mvuemba), Diop, Hughes, Traore, Crouch, Kanu (Davis)
Subs not used: Ashdown, Hreidarsson, Pamarot, Wilson
AC Milan: Dida, Zambrotta, Favalli, Senderos, Antonini, Gattuso (Seedorf), Emerson, Flamini, Kaka (Alexandre Pato), Inzaghi, Shevchenko (Ronaldinho)
Subs not used: Kalac, Kaladze, Pirlo, Bonera
