Just typing the title makes my fingers convulse. They’re looking at me like ‘are you sure, mate?!’ And I’m encouraging them to keep typing. Come on fingers, I’m not making this up; it happened, honestly.
On Thursday 27thNovember 2008, the red and black of AC Milan flew into Southampton Airport Parkway and took a coach up the M27. Ronaldinho was mobbed for autographs as the side waited for their luggage, and Pipo Inzaghi probably daydreamed of breaking the European goalscoring record, which he could do if he scored later on that day against Portsmouth.
At the age of 35, you would have been forgiven for thinking he was winding down, but even two years later he was scoring a brace at San Siro against a Jose Mourinho Real Madrid side in the Champions League, to take him to 70 European goals and level with Raul. Raul would go on to score 7 more, whilst that proved to be Inzaghi’s last two, but football aliens Lionel Messi and Cristiano Ronaldo would later come along and make a mockery out of perfectly respectable tallies by smashing in 113 and 129 and counting.
Whilst ‘Ronnie’ signed a stewardess’s blouse – yes, that did happen - and Inzaghi pondered, Andrea Pirlo lounged around looking suave, which is what he’d do for 90 minutes on the bench at Fratton Park later that evening, and Gennaro Gattuso got angry at a passing cloud.
Just two miles away, Wellington Sports Ground, owned by local private school King Edward VI, was host to Portsmouth as their de facto training ground. As Andriy Shevchenko and World Cup winner Dida made small talk with World Cup winner Kaka and World Cup winner Gianluca Zambrotta, Glen Little and Richard Hughes prepared for the game at a training facility that the club didn’t even own themselves.
(In case you were wondering, there were seven World Cup winners in Milan’s squad that day.)
Hughes had more reason than most to get excited about the glamourous tie. Having grown up in Italy as an AC Milan fan, Hughes was in the youth academy at Atalanta before moving to Arsenal in 1993. Fifteen years later, he was lining up against the man he idolised in his youth.
“I’m getting goosebumps talking about it,” Hughes told Portsmouth’s local newspaper The Newsin 2016, “the drive into the game was surreal.”
“I’m going to play against Milan. I’m going to play against Milan! I’d celebrated every goal with Pippo Inzaghi and we ended up being Inzaghied by Inzaghi.”
By the time the evening came round and both squads were in the bowels of Portsmouth’s 21,100-capacity stadium, the weather was pretty chilly, and pre-match chatter had it on good authority that their star-studded opposition weren’t up for it. Ignore the fact Milan has highs of just 11 Celsius and lows of 4 in November, compared to Portsmouth’s 12 and 6, Dave with the transistor radio in Row H knows that Georgian Kakha Kaladze isn’t a fan of the cold; Georgia is renowned for its warm winters and that’s probably why he didn’t come on. Probably.
Hang about Dave with the transistor radio, you might be right! Come half-time Inzaghi had flirted with the Portsmouth goal, but for now was being batted away by the woodwork, denied by both the post and the crossbar. As for Shevchenko, well he was nowhere to be seen. Probably somewhere in Sylvain Distin’s pocket – the pockets football shorts are notorious for. No, Milan were not having it easy and at the break Tony Adams could jig a merry jig in the dressing room and send his charges out to do the same again.
“Who are ya?! Who are ya?!” rang the chant from the Fratton faithful as Kaka wiggled his hips through the Portsmouth left before overhitting a cross out of play. Kaka was probably wondering himself. The other songs of the night heavily revolved around Adams, who was still searching for his first home win since taking over from Harry Redknapp, who had departed for Tottenham at the beginning of the month.
Adams was living a spirited existence on the sidelines, making every tackle with his defenders and every pass with his midfielders. Just after the hour mark, Adams stretched up onto his tippy toes and nodded in a delicate Glen Johnson cross, Younes Kaboul with the actual on-pitch goal.
“I remember going nuts when we scored our first goal – total surprise,” Portsmouth fan Tom, a season-ticket holder that year, told the Terrace. “The second was more disbelief.”
That’s right, Portsmouth scored twice that night; Johnson again assisting with a cross, this time for Kanu to scramble in.
“I thought we could hold on,” Tom added, “then Ronnie came on and changed the game.”
Newly-arrived from Barcelona, Ronaldinho was following in the footsteps of Rivaldo, who had joined AC Milan from Barcelona in 2002, and Ronaldo, who spent the 2007/08 season there, to complete the holy trinity of the World Cup 2002 lining up for the Italians. It was his free-kick that brought the game back within his side’s reach in the 84thminute.
“I was disappointed with the freekick. It was well executed because [David] James took a step behind the wall and got beaten on his side – something he did in the FA Cup Final when Drogba scored a freekick to beat us in 2010 too,” Tom remembers of the day, at which point he was 14-years old, “and it was absolute heartbreak when they scored the equaliser.”
If James was partly to blame for the first, his defence were at sea – only 1.8 miles away from the stadium, to be fair - for the second. Inzaghi ghosted in, a phrase he probably should have trademarked about ten goals into his career return of 288, and levelled the score to 2-2 in injury time.
“I watched it the other day and was still asking myself why no one was near him,” Hughes said eight years on from that incredible night, “what an experience, though. The highest of the highs. They were all there that night, and we were better than them.”
For Tom, over ten years on, it remains his favourite ever game as a Pompey fan.
“To draw against that team was still phenomenal, considering the quality of the players in each side. I think the most memorable thing was just the atmosphere and my inability to speak the next day. I am pretty sure I wore my Pompey shirt under my school shirt.”
“The day of the game or after?” I ask. “both.”