Now primarily known for his punditry and expert analysis across a range of broadcasters and outlets, it can be easy to overlook just how influential a figure Jamie Carragher was on Merseyside throughout a lengthy and distinguished playing career that lasted almost two decades.

Famously a boyhood Evertonian, Carragher was picked up by Liverpool in 1988, although he was fearless in continuing to wear his favourite Graeme Sharp Everton kit to training. In 1996 he helped lead the Reds to FA Youth Cup glory, overcoming a West Ham United side that featured Rio Ferdinand and Frank Lampard in the final.

That same year, his chance to make an impression in the first team finally arrived. He seized the opportunity and never looked back, going on to make 737 appearances for Liverpool in all competitions, second only to Ian Callaghan, as well as a club-record 149 appearances in European competition, where he experienced some of his biggest battles.

In an interview with Sky Sports back in 2020, Carragher was asked to name a team consisting of the 11 most difficult players he had faced. Here's who he selected.

Goalkeeper and Defence: Gianluigi Buffon, Cafu, Marcel Desailly, John Terry, Paulo Maldini

Few would dispute the inclusion of legendary Italian goalkeeper Gianluigi Buffon between the posts. A fierce competitor with an extraordinary career spanning almost 30 years, the Italian is among the select group of players to have made more than 1100 professional appearances. On Buffon, Carragher said:

"Goalkeeping wise, I've picked Gianluigi Buffon. I was born on the same day as him and scored against him, so it always gives me a chance to get that story in."

Buffon has been named Italian goalkeeper of the year a record 13 times and was also selected in the UEFA Team of the Year on five occasions, while finishing second in the 2006 Ballon d’Or, an award that has only been won by a goalkeeper once.

Cafu is widely considered one of the greatest right backs in football history, a position he dominated and helped redefine during an illustrious 19-year career. The football icon remains Brazil’s most-capped player with 142 international appearances to his name.

On the opposite flank stands Paulo Maldini, a player whose reputation alone was enough to intimidate opposing attackers. Maldini, as Carragher has acknowledged, is truly one of the greats. Equally capable at left back or in the centre, and like Carragher a one-club man, Maldini spent 25 years with AC Milan, much of that time as captain, winning an incredible 26 career titles.

Both Cafu and Maldini are well known to Carragher because of his role in the unforgettable 2005 UEFA Champions League Final in which the Reds rose from the dead to recover a 3-0 deficit and defeat Milan on penalties. The pair eventually gained revenge when Milan overcame Liverpool in the 2007 Champions League final.

The centre-back role is particularly interesting given Carragher’s own experience in the position, and the former Liverpool defender has singled out commanding Frenchman Marcel Desailly as one of the finest to play there. By the time Desailly arrived in the Premier League, the now-retired legend had already accumulated an impressive CV, winning the Champions League with Marseille in 1993 before claiming the trophy again the following season with AC Milan, becoming the first player to win the coveted competition in successive seasons with different clubs, this time operating as a defensive midfielder.

Alongside Desailly, Carragher selected his fellow countryman, John Terry. The Chelsea icon was named UEFA Defender of the Year in 2005, 2008, and 2009 and was a key figure in the Jose Mourinho side that completed an entire Premier League campaign while conceding only 15 goals, a record that remains intact. Carragher played alongside Terry for England 22 times, most notably at the 2006 World Cup in Germany and South Africa 2010.

Midfield: Roy Keane, Andres Iniesta, Xavi

At the base of midfield, Carragher has selected the central figure in one of football's great rivalries, former Manchester United star and fellow Sky Sports colleague Roy Keane. The 67-cap Republic of Ireland midfielder is sometimes overlooked by Premier League supporters but has always commanded enormous respect from fellow professionals, with Carragher being no different.

In front of Keane, Carragher selected one of the most iconic midfield partnerships of the 21st century - Barcelona pair Andres Iniesta and Xavi. Together, the Spaniards made 947 appearances for the Catalan club and 264 for their country, with both winning La Liga nine times, the Champions League four times, the UEFA European Championships twice and the World Cup once in 2010, when Iniesta scored the decisive injury-time winner. Once they had possession, getting it back was a serious challenge.

Attack: Lionel Messi, Thierry Henry, Cristiano Ronaldo

Attackers do not get much more formidable than Carragher’s trio of Lionel Messi, Thierry Henry, and Cristiano Ronaldo, so it is hardly a shock that these are the three players the Liverpool defender found most difficult to face.

What else is there to say about Messi? After winning the World Cup with Argentina in 2022, the little magician has collected virtually every major honour available. Now playing at a more relaxed pace in Miami, the Barcelona legend is entertaining a different audience. Carragher came up against the Argentine only twice, across a two-legged round of 16 tie in the 2006/07 Champions League campaign. Liverpool advanced to the quarter-finals on away goals and eventually reached the final, while most importantly for Carragher, he prevented ‘Leo’ from finding the net.

Henry and Carragher crossed paths much more regularly during the Frenchman’s iconic eight-year spell with Arsenal, meeting 16 times in total, with Liverpool winning six, losing seven and drawing three across all competitions, including the thrilling 2001 FA Cup final that ended in victory for the Reds. Henry departed the Premier League for Barcelona in 2007 after registering 174 goals in 254 league appearances, leaving a legacy that remains difficult to equal.

And then there is Cristiano Ronaldo. The Portuguese superstar possesses a collection of honours and records that few players can rival, along with a European legacy arguably unmatched by anyone else. At time of writing, he has the most Champions League appearances (181), the most Champions League goals (141), the most Champions League assists (42), the most goals in European Championship history (14), and more international goals than anyone (146).