When Richard Hughes knocked Liverpool out of the FA Cup

Richard Hughes is set to start work as Liverpool's new sporting director in the summer, joining the club as part of a restructured approach under the returning Michael Edwards.

Hughes will depart Bournemouth at the end of the season, having been first-team technical director at the south coast club since 2016 and part of the recruitment department since 2014.

His arrival in Liverpool's fresh structure, which will also see a new manager replace Jurgen Klopp, comes just over 20 years after Hughes enjoyed one of his greatest moments as a player by scoring a goal that knocked the Reds out of the FA Cup.

Hughes was born in Scotland, but the family was already based in Italy due to his father's career in publishing and as a youngster grew up in Milan. He turned down the chance to join AC Milan's youth ranks in 1989 when the club was at the peak of its powers as Europe's dominant force, but wound up joining Atalanta a few years later. His youth career then continued at Arsenal, although a first-team appearance for the Gunners never materialised before a 1998 transfer to Bournemouth.

The Cherries were a third-tier club at the time, far removed from the Premier League riches of 2024, but Hughes sufficiently impressed to earn a £50,000 transfer to Portsmouth in 2002 at a time when Harry Redknapp was building a team for a top flight promotion charge.

Hughes was ultimately primarily a squad player at Portsmouth, even spending part of his first season on loan at fellow second tier side Grimsby Town. But he was a reliable performer who was kept on for the entirety of the club's tumultuous seven-year run in the Premier League.

As a defensive midfielder, goals were not his strength. In fact, in 114 Premier League appearances, he didn't find the net once. Knowing that his main job was to prevent goals, Hughes has previously admitted holding onto other notable moments from his career – like the time he was headbutted by Cristiano Ronaldo, an incident which saw the then Manchester United winger sent off.

"It was a trivial moment. One of the highlights of my career, but an insignificant encounter for Cristiano Ronaldo," he recalled in 2021. "Should I ever meet people who don't necessarily remember me playing Premier League football, I can always tell them that one of the game's greats headbutted me. Sir Alex Ferguson afterwards said Ronaldo shouldn't get involved with inferior players."

Sadly for Hughes, he wasn't in the matchday squad when Portsmouth won the FA Cup in 2008, while he was an unused substitute on their return to the final in 2010 when they were beaten by Chelsea.

Having found the net a little more freely during his early career for Bournemouth, Hughes scored his only league goal for Portsmouth in his final game for the club in December 2010. The effort against Leeds in the Championship was originally marked down as an own goal but was eventually awarded to the five-cap Scotland international upon review by the dubious goals panel. The reason it was his last game for Portsmouth was purely down to the club's financial woes, with any further appearances after that entitling him to a new contract on higher wages that Pompey, having entered administration and been on the brink of liquidation earlier that year, couldn't afford.

Hughes initially retired aged just 32 but was persuaded to rejoin Bournemouth a year later, before hanging up his boots for good in 2014 and then moving behind the scenes.

Overall, he enjoyed a respectable but modest professional career, with a rare goal against his soon to be employers in February 2004 one of the undeniable highs. Although not a vintage Liverpool side, Gerard Houllier's Reds were heavy favourites after being drawn at home for the FA Cup fifth-round tie against a Portsmouth team in their first season back in the top flight. Despite enjoying nearly half a century of unbroken top-flight football between 1905 and 1953, Pompey had just one single further First Division season (1987/88) prior to their 2003 promotion and were underdogs.

Michael Owen scored in the first minute of the tie, but Matty Taylor snatched an equaliser with 15 minutes left to play, while Portsmouth also had goalkeeper Shaka Hislop to thank for his contribution in keeping Liverpool at bay as Redknapp's team simply fought to stay in the game.

The replay at the more intimate but equally atmospheric Fratton Park a week later was another game Liverpool ought to have won given their domination. Hislop was again in top form and denied Owen from the penalty spot in the second half, controversially awarded for Taylor's challenge on Milan Baros in which he had appeared to play the ball. The Portsmouth goal shortly afterwards was out of the blue, but that didn't matter to the vocal home fans on the south coast.

Hughes didn't start the game, instead brought on at half-time in place of defender Dejan Stefanovic, but found himself in the right place at the right time to make the decisive impact. Sami Hyypia was guilty of losing the ball in Liverpool's half, his pocket picked by Eyal Berkovic. The ball was played out to Kevin Harper on the right, who in turn found Alexei Smertin. The Russian's first-time pass went to Yakubu, who had clearly already seen Hughes in space to the left of the box and quickly laid the ball into his path. Liverpool right-back Steve Finnan had been sucked into the middle to cover Nigel Quashie's run forward, leaving Hughes with all the time in the world to take a touch and fire low across the goal, beyond the reach of goalkeeper Chris Kirkland.

Qualifying for the quarter-finals, Portsmouth didn't go any further in the FA Cup that season thanks to a 5-1 demolition at Fratton Park at the hands of Arsenal. Hughes was again a substitute but was introduced for the final 20 minutes when the Gunners were already five goals ahead. Liverpool also got revenge with a 3-0 Premier League win over Portsmouth at Anfield a few weeks later. Yet that day in the cup helped spark something in Pompey that ultimately kept them in the Premier League.

At that time, Portsmouth had won just five of their 25 league games and were only out of the relegation zone on goal difference. But they drew their next Premier League fixture against a Newcastle United side on course to qualify for the Champions League for the second year running courtesy of a late Lomana LuaLua equaliser. Following back-to-back defeats against Everton and Liverpool on Merseyside, Portsmouth then lost only one of their remaining ten games, winning six and claiming 21 points from a possible 30 to fly up the table to 13th by the campaign's conclusion.

As a back-up, Hughes' role on the pitch during that run was minimal, but his moment of FA Cup glory against Liverpool, the club where he will soon play an active role in building the future, played its own part in a way, as well as creating a historic memory of the moment itself.

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