Jump directly to the content

News Corp is a network of leading companies in the worlds of diversified media, news, education, and information services.

DREAM TEAM

Your Sun

A News UK Company
TOP
ONE NIGHT IN PORTSMOUTH

Remembering when AC Milan’s world-class spine failed in the last ever UEFA Cup

AC Milan were involved in the last UEFA Cup competition before it turned into the Europa League, but how much can you remember about that campaign?

The mere mention of the UEFA Cup is enough to make us weak at the knees with nostalgia.

Throw in an AC Milan side containing Paolo Maldini, Kaka, Andriy Shevchenko, Filippo Inzaghi and Gianluca Zambrotta, among others, and we’re struggling to think straight.

But Milan’s 2008/09 UEFA Cup campaign- the last instalment of the tournament before it became the Europa League- didn’t live up to the hype.

For anyone who can’t remember their glorious failure remember, here’s a recap.

EXCLUSIVE OFFER: BET £5, GET A FREE £20 BET

Don’t look so scared lads, it’s only Portsmouth

PA:Press Association
7
Don’t look so scared lads, it’s only Portsmouth

Carlo’s core

Think of Carlo Ancelotti’s reign as Milan manager and certain players come to mind.

Zambrotta and Maldini in defence, Andrea Pirlo, Kaka, Clarence Seedorf and Gennaro Gattuso in midfield, with Shevchenko and Inzaghi up front.

All were present during Milan’s last UEFA Cup campaign, as were Alexandre Pato, Alessandro Nesta, David Beckham and Ronaldinho.

In short, Carlo wasn’t struggling for players to choose from.

We’d be taking it pretty easy as well if we had all those players to pick from

PA:Empics Sport
7
We’d be taking it pretty easy as well if we had all those players to pick from

The world’s best agent

Scratch beneath Milan’s seemingly endless supply of world-class players and one defender stood out.

This was no average defender. In fact he was a little bit below average.

We’re talking about none other than Philippe Senderos, who found himself on a season-long loan from Arsenal, surrounded by some of European football’s great and good.

Whoever his agent was, you deserve a very large pat on the back. You should probably also be working on Brexit with those negotiating skills.

Name a more iconic duo

7
Name a more iconic duo

One night in Fratton Park

Milan were drawn in Group E alongside Heerenveen, Braga, Wolfsburg and Portsmouth. After wins against the first two, it was time for a trip to the south coast.

A fraction over 20,000 people crammed in to Fratton Park to see Tony Adams’ side go up against Ancelotti’s elite.

Younes Kaboul marking Shevchenko, Richard Hughes man-marking Kaka and Ronaldinho, Peter Crouch and Kanu trying to get the best of Dida. Sensational.

Bet Ronaldinho will never forget that night as long as he lives

Times Newspapers Ltd
7
Bet Ronaldinho will never forget that night as long as he lives

With 83 minutes on the clock the unthinkable was happening. Portsmouth were two goals to the good thanks to Kaboul and Kanu.

A minute later Ronaldinho halved the deficit but, as 90 minutes trickled over on the clock, Pompey tried to hold firm.

However Inzaghi, a man born to score one-yard scuffles from offside positions, had to spoil the fun by equalising from the penalty spot. Bah humbug.

Are you sure he wasn’t offside?

Times Newspapers Ltd
7
Are you sure he wasn’t offside?

From Peru with goals

Milan secured a somewhat shaky route to the knockout rounds with a draw against Wolfsburg, only to find themselves facing more German opposition in the shape of Werder Bremen.

A goal from maverick no.10 Diego rescued Bremen a draw in Germany after Inzaghi put Milan ahead, meaning it was winner takes all in the San Siro.

Ancelotti kept Shevchenko on the bench and started Pato- a decision that looked inspired when he made it 2-0 on the night five minutes after a Pirlo penalty.

But Bremen’s talented side, featuring Mesut Ozil, Per Mertesacker, Torsten Frings and Naldo, struck back with two Claudio Pizarro headers in the second-half.

Milan were out.

The look on Maldini’s face said it all

7
The look on Maldini’s face said it all

Goodbye gaffer

The 2008/09 season would be Ancelotti’s last as Milan manager.

He was replaced by Leonardo in the summer, with Maldini, Emerson and Kaka also leaving the San Siro.

Ancelotti took over at Chelsea and led them to a Premier League title at the first try, becoming the first team to do so while scoring more than 100 goals.

As for Portsmouth, they were relegated- the beginning of a slide that now sees them playing in the third tier of English football, a million miles away from Kaka, Ronaldinho and Inzaghi.

It’s a funny ol’ game.

We couldn’t go an entire article without including a picture of Becks

AP:Associated Press
7
We couldn’t go an entire article without including a picture of Becks

EXCLUSIVE OFFER: BET £5, GET A FREE £20 BET