Football Features

Portsmouth 2-2 AC Milan, when Adams went up against Ancelotti

By Squawka News

Published: 16:20, 30 July 2021

Portsmouth are preparing for their fourth season in League One, the third tier of English football, a far cry from their Uefa Cup run in 2008.

After winning the FA Cup Portsmouth went on a European tour and in November 2008, Italian giants AC Milan travelled to Fratton Park to take on Tony Adams’ Pompey. Considered minnows compared to their experienced and well-decorated opposition, Portsmouth more than held their own and were mere moments away from claiming a shock win over Carlo Ancelotti’s outfit.

With all the goals coming in the second half of the match, it was Portsmouth who took the lead after 62 minutes from a Younès Kaboul header. Things got even better for the south coast side when former Arsenal centre-forward and FA Cup hero Nwankwo Kanu bundled the ball home in the 73rd minute to double Portsmouth’s lead.

Despite Portsmouth’s best efforts to preserve their lead with just 17 minutes to go, the quality of AC Milan eventually made its way onto the Fratton Park pitch. Goals from Brazilian wonder Ronaldinho and striking sensation Filippo Inzaghi – the latter scoring two minutes into injury time – broke Portsmouth hearts as the match finished as an entertaining score draw.

Here is what happened next to each player that played a part in that entertaining match.


David James

Age: 51

Current club: Retired

Portsmouth appearances: 158

The former England number one spent four years down on the south coast but he was never a man to settle down with one club and moved on in 2010 to Championship side Bristol City.

Spells at AFC Bournemouth, Icelandic side ÍBV Vestmannaeyjar and Indian Super League outfit Kerala Blasters followed before he eventually retired in 2014. He was offered his first chance at management in 2018 but was sacked by the end of the year following a string of poor results.

Portsmouth-AC Milan

Glen Johnson

Age: 36

Current club: Retired

Portsmouth appearances: 100

Portsmouth goals: 4

The West Ham United graduate moved to Portsmouth following his unsuccessful spell at Chelsea. After reaching the 100 mark at Fratton Park, Johnson moved to Liverpool where he was part of the side that narrowly missed out on the Premier League title in the 2013/14 season.

200 appearances and a Football League Cup trophy later, Johnson left Merseyside to join Stoke City where following their relegation at the end of the 2017/18, he was released. He subsequently retired.

Younès Kaboul

Age: 35

Current club: Retired

Portsmouth appearances: 50

Portsmouth goals: 5

The big centre-back was the man to put Portsmouth ahead on this fateful night. Despite signing a four-year contract with Portsmouth in 2008, by January 2010 he was back at Tottenham Hotspur with the two clubs agreeing on a £9.5 million deal.

Five years at Spurs followed before moving to Sunderland where Kaboul was part of Sam Allardyce’s Sunderland side who escaped relegation in 2016. He then moved to the Hornets for £4 million where he was mainly found outside of the starting eleven before leaving the club by mutual consent in December 2018. Having left Watford in 2017, he retired soon after.

Sylvain Distin

Age: 43

Current club: Retired

Portsmouth appearances: 96

Portsmouth goals: 0

The classy left-footed defender was a man mountain at the heart of the Portsmouth defence and was a big part of the club’s success throughout his tenure.

Distin played for some notable clubs before his move to Portsmouth including the likes of Paris Saint-Germain, Manchester City, Newcastle United. Distin left Fratton Park to join Everton in 2009 before playing for Bournemouth in 2015 and later retiring.

Portsmouth vs AC Milan

Nadir Belhadj

Age: 38

Current club: CS Sedan Ardennes

Portsmouth appearances: 65

Portsmouth goals: 6

The Algerian, who used to give Adams ‘heart attacks’ for his lack of defensive quality, first moved to the club on a season-long loan before moving permanently following a successful spell.

With 55 caps for his country, Balhadj left the club in 2010 for Al-Sadd before trying his luck at both Al-Sailiya and Sedan, rejoining the latter in 2021.

Glen Little

Age: 45

Current club: Retired

Portsmouth appearances: 8

Portsmouth goals: 0

The right winger has enjoyed a long career in football and is perhaps better known for his spells at Reading and Burnley rather than his time at Portsmouth.

Released after one season at the club, Little did the rounds in the lower leagues, getting involved in football for Grays Athletic as player/assistant manager. He also had a short spell as manager of Wingate & Finchley.

Portsmouth-AC Milan

Papa Bouba Diop

Portsmouth appearances: 72

Portsmouth goals: 0

One of the standout stars of the 2002 World Cup three years previous, Diop joined Portsmouth from fellow Premier League outfit Fulham and went on to only leave the club following their relegation in 2010.

Stints for AEK Athens, West Ham United and Birmingham City followed before Diop bowed out of the game. Diop sadly died in November 2020 following a long illness.

Richard Hughes

Age: 42

Current club: Retired

Portsmouth appearances: 157

Portsmouth goals: 2

The midfield man was a solid player in the middle of the park for Portsmouth across nine years of service before moving on to pastures new.

Two years at fellow south coast side Bournemouth followed before Hughes decided to hang up his boots in 2014 with five Scotland caps to his name.

Armand Traoré

Age: 31

Current club: Free agent

Portsmouth appearances: 28

Portsmouth goals: 1

Traore could play anywhere on the left which he did so for a number of clubs across his well-travelled career.

One season on loan at Portsmouth from parent club Arsenal was followed by showings for Juventus (on-loan), Queens Park Rangers, Nottingham Forest, Cardiff City (on-loan) and Turkish side Çaykur Rizespor.

Traore returned to Cardiff in 2019 but was released having not played a single match.

Peter Crouch

Age: 40

Current club: Retired

Portsmouth appearances: 86

Portsmouth goals: 33

Portsmouth-AC Milan

Everyone’s favourite robot machine, Crouch had already established himself as a talented Premier League striker for a number of clubs before his second spell at Fratton Park.

Two years at Tottenham Hotspur followed where he scored the goal away at Manchester City that got them into the Champions League in May 2010. After an eight-year stay with Stoke City and a short stay with Burnley, Crouch retired in 2019.

Nwankwo Kanu

Age: 45

Current club: Retired

Portsmouth appearances: 168

Portsmouth goals: 28

A goal on the night against AC Milan was thought to seal the win for the hosts but it just wasn’t meant to be. However, Kanu did score the only goal months earlier to seal Portsmouth’s FA Cup victory over Cardiff City at Wembley.

Important goals rather than lots of them, Kanu left the club in 2012 following a dispute over unpaid wages that the club reportedly owed him and is now retired.

Portsmouth-AC Milan


Arnold Mvuemba

Age: 35

Current club: Roeselare

Portsmouth appearances: 32

Portsmouth goals: 2

Mvuemba spent a short time with Portsmouth between 2007 – 2009 with the one-cap DR Congo international failing to establish himself as a first-team regular for the club.

Successful spells with Lyon and Lorient once again led him to sign for Qatar side Umm Salal. He most recently turned out for Roeselare in Belgium but left in July and is now playing for Roeselare in Belgium.

Sean Davis

Age: 41

Current club: Retired

Portsmouth appearances: 116

Portsmouth goals: 4

The midfielder enjoyed great spells with Fulham and Portsmouth, notching over 100 appearances for both sides.

An injury-laden few years followed his exit from Portsmouth meaning Davis couldn’t reignite his career at either Bolton Wanderers or Bristol City. He retired in 2012.

AC Milan


Age: 47

Current club: Retired

AC Milan appearances: 302

Dida was known as one of the best shot-stoppers in European football and enjoyed a highly decorative career both domestically and on the international stage.

After his 10 years of service in Milan, Dida moved back to his native country to play for Portuguesa, Grêmio and Internacional before retiring soon after.

Gianluca Zambrotta

Age: 44

Current club: Retired

AC Milan appearances: 107

AC Milan goals: 2

It was at Serie A rivals Juventus where Zambrotta truly made his name, helping him win a massive 98 caps for Italy across a space of 11 years.

Four years in Milan for one of Europe’s most recognised full-backs, Zambrotta saw out his footballing days with Chiasso before taking over as their manager in 2014. However, he was eventually sacked in April 2015.

Giuseppe Favalli

Age: 49

Current club: Retired

AC Milan appearances: 99

AC Milan goals: 2

The left-back spent his entire footballing career in Italy playing for just four clubs including Milan between 2006 – 2010.

Not long after the match against Portsmouth, Favalli was released by the club and as a result, he decided to retire from professional football altogether.

Philippe Senderos

Age: 36

Current club: Retired

AC Milan appearances: 20

AC Milan goals: 1

Perhaps you forgot that Senderos was once part of one of Europe’s greatest defence after he left north London side Arsenal for Milan on a season-long loan in 2008.

The Swiss international didn’t play too many games for Ancelotti’s side before moving on and after playing for different clubs in England, as well as Rangers and MLS side Houston, Senderos finished his career with FC Chiasso in his homeland.

Portsmouth-AC Milan

Luca Antonini

Age: 38

Current club: Retired

AC Milan appearances: 111

AC Milan goals: 1

Antonini was your traditional tough Italian defender who made life difficult for the opposition throughout his five years playing for Milan.

Winning the Serie A title in 2010-11, Antonini moved on and played for Genoa, Ascoli, Livorno (on-loan) and Prato before he retired in 2016.

Gennaro Gattuso

Age: 43

Current club: Retired

AC Milan appearances: 467

AC Milan goals: 11

Everyone remembers Gattuso as that tough-tackling, no-nonsense midfielder who would pick a fight with anyone, including Portsmouth assistant manager Joe Jordan!

13 years at the club turned Gattuso into a club legend which was why after his retirement it was fitting to see him take charge of the club in a managerial capacity. Unfortunately, that job only lasted 83 games after he left in May 2019. But he landed on his feet and is now in charge of Napoli where he had them looking like a serious side again before leaving in the summer. Gattuso then spent 23 days in charge of Fiorentina before leaving, without taking charge of a single game.


Age: 45

Current club: Retired

AC Milan appearances: 40

AC Milan goals: 0

Fratton Park witnessed one of the best defensive midfielders around at that time when Emerson came into town.

The genius Brazilian left Milan in 2009 to join Santos before finishing his career at Miami Dade FC.

Mathieu Flamini

Age: 37

Current club: Free agent

AC Milan appearances: 122

AC Milan goals: 8

Another former Arsenal man in the Milan ranks, Flamini spent five years in Italy where he too was a part of the Serie A 2010/11 title-winning side.

Spells at Crystal Palace and Getafe followed. Currently he is without a club and, although not officially retired nowadays he spends more time focusing on the company he co-founded, GF Biochemicals.

Flamini’s company are the first company ever to mass-produce levulinic acid – a compound that could hold the key to unlocking the potential of biofuels. From protecting the Arsenal defence to protecting the planet? Arsene would be proud!

Portsmouth-AC Milan


Age: 39

Current club: Retired

AC Milan appearances: 307

AC Milan goals: 104

The classy Brazilian was awarded the Ballon d’Or award for his performances throughout 2007, meaning one of the best players in the world had graced the pitch at Fratton Park.

Admired throughout his career as one of the best attacking midfielders of his generation, the 2002 World Cup winner moved to Real Madrid, had a second spell at Milan before eventually retiring after some time in MLS with Orlando City.

Filippo Inzaghi

Age: 47

Current club: Brescia (Manager)

AC Milan appearances: 300

AC Milan goals: 126

One of the greatest goalscorers of his generation. This Milan side was truly littered with some of the best strikers in world football at the time and Inzaghi was most definitely one of them.

The Italian never played for anyone else and retired from football in 2012. He is currently the manager at Italian side Brescia, joining them after a two-year spell in charge of Benevento in which he had achieved promotion to Serie A for only the second time in the club’s history.

Portsmouth-AC Milan

Andriy Shevchenko

Age: 44

Current club: Ukraine (Head coach)

AC Milan appearances: 322

AC Milan goals: 175

See what we mean about attacking talent and trust us, we’re not even finished yet!

Two extremely successful spells with Milan, an unsuccessful stint at Chelsea and two more fantastic periods spent with Dynamo Kyiv later, Shevchenko’s career will be remembered by many. He is now in charge of the Ukraine national side and has even taken a stab at politics!


Clarence Seedorf

Age: 45

Current club: Retired

AC Milan appearances: 432

AC Milan goals: 62

Another world-class star among this Milan squad. Despite the late equaliser, it’s making Portsmouth 2-2 draw with them seem even more impressive isn’t it?

Seedorf is already considered a fairly experienced manager, with his natural intelligence leading the likes of Milan, Shenzhen, Deportivo La Coruña and, most recently, Cameroon in his short but busy managerial career to date.


Age: 41

Current club: Retired

AC Milan appearances: 95

AC Milan goals: 26

World-class, well-loved, and really, really talented; Ronaldinho had it all.

After leaving Milan in 2011, Ronaldinho spent the rest of his career in Brazil playing for Flamengo, Atlético Mineiro, Querétaro and Fluminense before retiring in 2018. Since then he’s partied hard, played futsal in India, endorsed fascism and spent time in a Paraguayan jail.

Alexandre Pato

Age: 31

Current club: Orlando City

AC Milan appearances: 150

AC Milan goals: 63

A youngster among experienced pros, Pato was once labelled as one of the most promising strikers in world football.

His career, although decent enough, has failed to live up to those high standards expected from him and he is one of a few players who opted to move to China for the lifestyle and financial rewards after trying his luck in Europe with Milan, Chelsea and Villarreal.

His time in Asia yielded 36 goals in 60 games. Pato returned to Brazil with Sao Paulo, but has since left, and at 31, currently finds himself in MLS with Orlando City.