Liverpool face Barnsley in the FA Cup on Monday night, with memories still lingering of the last meeting between the sides, when the Tykes stunned the Reds with an unforgettable win
Harry Kewell in action vs Barnsley
Liverpool were famously knocked out of the FA Cup by Barnsley in 2008(Image: Photo by Alex Livesey/Getty Images)
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It's been 18 years since Liverpool suffered a shocking FA Cup embarrassment at the hands of Barnsley - their opponents this evening. The Reds lost 2-1 at Anfield in one of the biggest upsets of the season.
Despite having Champions League winners in their ranks and Steven Gerrard on the bench, Rafa Benitez's side couldn't overcome The Tykes, who were in the Championship at the time. Liverpool initially took control thanks to a goal from Dirk Kuyt but strikes by Stephen Foster and Brian Howard sealed what remains one of the greatest shocks in FA Cup history.
Barnsley keeper Luke Steele, drafted in on an emergency loan from West Brom, produced an outstanding display to deny Liverpool's star names. It's worth remembering this upset came just three years after the Reds had achieved the miracle of Istanbul.
The two clubs meet again in the FA Cup third round on Monday evening, with the south Yorkshire side hoping to relive that famous upset. Liverpool's form has been wobbly over the past few months but Barnsley are struggling near the foot of League One, making Arne Slot's side clear favourites.
In goal that day was Cameroon international Charles Itandje. Now 43-years-old, he has most recently been named as the goalkeeping coach at FC Versailles.
The central defensive partnership consisted of Sami Hyypia and Jamie Carragher. Hyypia, a Finnish icon, tried his hand at management with Bayer Leverkusen, Brighton and FC Zurich, though he has not held a managerial role for more than five years.
These days he acts as an official Liverpool ambassador and also spends time involved in motor sport. Carragher, meanwhile, has forged an outstanding media career and is a regular pundit on Sky Sports and CBS.
At full-back were Steve Finnan and John Arne Riise. Riise has remained active in the game, managing Norwegian club Avaldsnes in 2023 and frequently appears on the Liverpool Legends circuit.
John Arne Riise on the ball vs Barnsley
John Arne Riise (pictured) was one of several high-profile Liverpool stars who started that day(Image: Photo by Alex Livesey/Getty Images)
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Finnan moved into property after hanging up his boots and has largely lived off-grid since retirement. However, he later became embroiled in a legal dispute with his brother and is now reportedly facing bankruptcy.
A cult hero at Anfield, Yossi Benayoun later represented Chelsea and Arsenal, enjoying a solid spell at the top level. He retired in 2019, with his latest role being sporting director of the Israel national team, a position he left in 2024.
The midfield pairing on the day was Xabi Alonso alongside Lucas Leiva. Alonso is currently the manager of Real Madrid, following a hugely impressive spell in charge of Bayer Leverkusen. Lucas was forced to retire in 2023 due to a heart condition and is now enjoying life away from football.
Ryan Babel, who, like Benayoun, featured on the wing that day, only called time on his playing career at the end of 2024. He boasts a huge audience on YouTube and Instagram and also has strong links within the fashion world.
Barnsley players celebrate with their fans after the team's victory over Liverpool in the FA cup
Barnsley will be hoping for a repeat of the result they clinched at Anfield back in 2008(Image: Getty Images)
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Up front, Peter Crouch partnered Dirk Kuyt. Crouch has become a major television figure, appearing regularly on TNT Sports and hosting the highly successful podcast - The Peter Crouch Podcast. Along with Carragher, he has arguably enjoyed the most prominent post-playing career from this squad.
Kuyt moved into coaching after retiring. Following spells with ADO Den Haag and Beerschot, he was appointed head coach of FC Dordrecht in the summer of 2025.
Gerrard and Harry Kewell were the only substitutes to be introduced. Gerrard has since managed Rangers, Aston Villa and, more recently - Al-Ettifaq. He left that post in January 2025 and is now searching for his next opportunity.
Kewell has remained in coaching continuously since 2017, with roles at Crawley Town, Notts County, Oldham Athletic and Barnet. He later took on a challenge in Japan with Yokohama F. Marinos, before being named head coach of Vietnamese side Hanoi FC in October 2025.
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