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15th December 2015
04:15pm GMT
Blackburn were the main beneficiaries, with Friedel making almost 300 appearances for Rovers in almost eight years, before further successful spells at Aston Villa and Tottenham.
Given the fact that he only recently retired, there are plenty of Reds supporters who feel that the 44-year-old would still represent a better bet in goal than Simon Mignolet.
Defender: Markus Babbel (Liverpool)
Liverpool's last German hero saw his time at Anfield wrecked by illness, with Babbel struck down by the debilitating Guillan-Barré Syndrome after an excellent first season in which he had helped the side to a treble of the UEFA Cup, the League Cup and the FA Cup.
Defender: Sol Campbell (Arsenal)
Arguably the most famous free transfer of all time, and undoubtedly the most controversial.
Former Tottenham defender Campbell won the Premier League and FA Cup double during his first season with Arsenal in 2001/2002, and would form a brick wall of a defence with Kolo Touré during the 'Invincibles' season back in 2004.
Spurs fans still have not forgiven him, and never will.
Defender: Bacary Sagna (Manchester City)
A crafty piece of business by City to snap up free agent Sagna from Arsenal in the summer of 2014. This one looked like a bust as Sagna would only play nine Premier League games in his debut season at Eastlands, but he has cracked the first team to far better effect this season.
At 32 he remains one of the most solid full-backs in England.
Defender: Luis Enrique (Barcelona)
Possibly the only player to have been both adored by both Real Madrid and Barcelona fans, although that may have changed since he took over the manager's job at the Nou Camp.
Enrique left the Bernabeu on a free transfer in 1996 at the age of 26, moving to Real Madrid's massive rivals Barcelona and going on to win two La Liga titles and two Copas del Rey, as well as captaining the side.
Midfielder: Esteban Cambiasso (Inter Milan, Leicester City)
The scorer of the greatest goal in the history of the World Cup Finals was just 24-years-old when his contract at Real Madrid ran out and he joined Inter Milan, where he would remain for a decade and win five Serie A titles, four Coppas Italia and the Champions League in 2010.
One stellar free transfer turned to two in the summer of 2014 when the then 34-year-old Cambiasso joined Leicester City.
His contribution in his only Premier League season has been somewhat lost by the Foxes' ridiculous form this term, but Cambiasso was the crucial factor in Leicester maintaining their top flight status under Nigel Pearson.
Midfielder: Paul Pogba (Juventus)
Hindsight is 20-20 and all that, but letting Pogba run his contract down and join Juventus on a free registers as the last great mistake of Alex Ferguson's reign at Manchester United.
Still only 22, Pogba is arguably the most coveted young central midfield player in world football and destined for a move to one of the two big clubs in Spain, while United continue to play Marouane Fellaini on a semi-regular basis.
Midfielder: Gary McAllister (Liverpool)
This is the one that absolutely nobody saw coming, but represents the biggest managerial masterstroke of Gerard Houllier's time in charge of Liverpool.
When he joined Liverpool in the summer of 2000, nobody could have foretold the influence of the 35-year-old former Leeds and Coventry stalwart. However, a crucial derby winner against Everton and a man of the match performance in the UEFA Cup Final against Alaves were just two highlights of McAllister's time at Anfield, and he would become one of the club's all-time great cult heroes.
Midfielder: Andrea Pirlo (Juventus)
He cost Juventus nothing from AC Milan. Take some time to think about that.
Pirlo was always highly thought of at Milan but has taken on the status of icon since his move on a free transfer to the Old Lady in 2011. He won the Scudetto in each of his four seasons at the club before entering semi-retirement in the United States.
Forward: Robert Lewandowski (Bayern Munich)
A decent first season at Bayern saw Lewandowski plunder 17 Bundesliga goals, but this season the man who left Borussia Dortmund on a free in the summer of 2014 has been in phenomenal form.
With the injured Arjen Robben and Franck Ribery replaced by more traditional wingers Kingsley Coman and Douglas Costa, as well as Thomas Muller as a world class foil, the system suddenly suits the 27-year-old Pole and he has scored 29 goals for club and country since the start of August.
Forward: Roberto Baggio (Bologna)
They thought he was finished. He wasn't finished.
Baggio had endured a tough time at AC Milan and was no longer required by manager Fabio Capello in 1997. When Carlo Ancelotti turned down the chance to take the Divine Ponytail to Parma on a free transfer, Bologna lapped that s**t up and the 30-year-old went on to score 22 league goals.
Ancelotti called it the biggest mistake of his career.Explore more on these topics:
