Portsmouth hit the jackpot with £5m deal - 'one of the best players to ever wear a Pompey shirt' | OneFootball

Portsmouth hit the jackpot with £5m deal - 'one of the best players to ever wear a Pompey shirt' | OneFootball

In partnership with

Yahoo sports
Icon: Football League World

Football League World

·2 November 2025

Portsmouth hit the jackpot with £5m deal - 'one of the best players to ever wear a Pompey shirt'

Article image:Portsmouth hit the jackpot with £5m deal - 'one of the best players to ever wear a Pompey shirt'

FLW's Portsmouth fan pundit has given his verdict on the club's greatest £20m transfer masterstroke

This article is part of Football League World's 'Terrace Talk' series, which provides personal opinions from our FLW Fan Pundits regarding the latest breaking news, teams, players, managers, potential signings and more…


OneFootball Videos


Lassana Diarra spent just one season at Portsmouth but he made a memorable impact at the club before signing for Real Madrid.

It was reported that the Spanish giants paid £20 million to sign the midfielder in January 2009, just 12 months after he’d moved to Fratton Park for £5 million.

He made 24 league appearances for Pompey across his two half-seasons with the team, helping them finish eighth in the table in 2007/08.

Diarra was also a part of Harry Redknapp’s side as they won the FA Cup final against Cardiff City in 2008.

The Frenchman went on to be a regular member of the Real Madrid first team squad until his departure in 2012, going on to play for the likes of Marseille, PSG and Lokomotiv Moscow, among others, before retiring in 2019.

Lassana Diarra was Portsmouth’s biggest transfer masterstroke

Article image:Portsmouth hit the jackpot with £5m deal - 'one of the best players to ever wear a Pompey shirt'

When asked if the Diarra deal was one of the club’s best ever transfer moves, FLW’s Portsmouth fan pundit Miltos Ioannidis claimed it’s the greatest one of all.

He believes the midfielder is one of the best players to ever put on the shirt, and that he is very fondly remembered by supporters despite only spending one year at Fratton Park.

“Absolutely, without a doubt,” Ioannidis told Football League World.

“I may have been a bit too young to remember Lassana Diarra playing for Pompey.

“But from what I know of him, the player that he was, the fact that we managed, first of all to get him to the club, like Lassana Diarra to Pompey, and the fact that we then managed to make this remarkable, especially for that time, profit on him after just a year.

“He’s definitely, on paper, as a transfer, he’s definitely the biggest transfer masterstroke that this club has ever had.

“And, I think more importantly also, one of the best players that this club has ever had.

“One of the best players to ever wear a Pompey shirt.”

Ioannidis claimed that Diarra is still spoken of very highly among fans, and that he is one of the best footballers to ever play for the club: “Yes, I don’t remember him, but I see a lot of people nowadays speaking very highly of Diarra, saying that he was technically, footballing ability, the best player that they can remember.

“And I think he’s definitely right up there with one of the best to ever wear the shirt, definitely.

“I was only one-years-old when he joined Pompey, and obviously I wasn’t into football, I couldn’t have been into football at that time, but I know Diarra.

“I remember Diarra before he retired as well, and he’s definitely up there as one of the best players to wear a Portsmouth shirt, undoubtedly in my mind.”

Diarra started the 2008 FA Cup final, and was only substituted in stoppage time with the team set to clinch a 1-0 win over Cardiff.

The midfielder scored just two goals during his time at Fratton Park, with the strikes coming in a 1-0 win over Bolton Wanderers and a 2-0 victory over Vitoria in the UEFA Cup.

Article image:Portsmouth hit the jackpot with £5m deal - 'one of the best players to ever wear a Pompey shirt'

Lassana Diarra deal couldn’t save Portsmouth from financial disaster

The £20 million earned for Diarra was great business for Portsmouth, but this was also a period where financial issues began to really plague the club.

Pompey slipped from the Premier League to League Two in the years following their FA Cup win, with significant mismanagement issues causing the decline.

Multiple owners wasted massive amounts of money through Portsmouth, so it’s a shame that the great business with Diarra didn’t lead to anything but problems behind the scenes.

However, supporters will always remember his short time in the team very fondly, and no amount of financial issues can take away the glory of the 2008 FA Cup win.

View publisher imprint