
Tottenham Hotspur are exploring a move to sign Angel Di Maria ahead of his contract with Paris Saint-Germain ending in June, but how have Spurs’ recent free transfers worked out?
The north Londoners have rarely dipped into the Bosman market in recent years whenever looking to strengthen their ranks. Joe Hart was the last star to arrive at Tottenham without Spurs chairman Daniel Levy paying a fee when the goalkeeper joined from Burnley in 2020.
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Hart left Turf Moor after his contract lapsed and joined Jose Mourinho’s side to push Hugo Lloris and Paulo Gazzaniga. But Antonio Conte would be hoping Di Maria can push those at Tottenham already far more than Hart could with a free transfer from Paris Saint-Germain.

Tottenham eye free swoop for Paris Saint-Germain ace Di Maria
Reports by Calcomercato.it claim Di Maria’s entourage have made it clear he will not sign a new deal with PSG. Les Parisiens also anticipate separating at the end of his existing terms, worth €10m-a-year (£162k-a/w), in June. So, the Argentine’s camp are speaking to suitors.
Di Maria does not forget how intently Juventus and Inter Milan have previously pushed for his services. A move to Serie A would now please him a lot, so the 34-year-old’s agent has approached Juventus. But Di Maria’s camp have also been in touch with Tottenham chiefs.
The 121-cap international does not rule out a return to the Premier League after a year at Manchester United. But it has always been Di Maria’s intention to finish his career back in Argentina. So, he may only seek a one year contract this summer, with a 12-month option.
Tottenham tabling a one year contract to Di Maria, ahead of his Paris Saint-Germain terms expiring, would see the £44.5m ex-Red Devils man become just Spurs’ ninth free transfer since 2007. So, how did the north London outfit’s last eight freebies fair while at the club?

Joe Hart – Burnley to Tottenham, 2020
Hart spent two years at Burnley after leaving Manchester City in 2018 before joining Spurs in a free transfer. The 75-cap England goalkeeper had only enjoyed a brief stint as the first-choice between the sticks at Turf Moor after a torrid start to the goalkeeper’s debut term.
He allowed 41 goals in 19 games and did not feature in a league match between December 2018 and joining Spurs. Yet Hart only remained in north London for a season, in which he made all 10 appearances in cup competitions before joining Celtic in August 2021 for £1m.
Ryan Nelsen – Blackburn Rovers to Tottenham, 2012
Hart was Tottenham’s first free transfer in eight years, having last took Ryan Nelson to the capital in a Bosman from Blackburn Rovers in 2012. The Ewood Park outfit cancelled the defender’s contract just moments before that year’s January deadline day would conclude.
Harry Redknapp sought to strike an out-of-window deal for the New Zealander as he liked his competitive nature. Yet the centre-half only played eight times for Spurs, including just five Premier League games. He also made each of his top-flight appearances off the bench.

Louis Saha – Everton to Tottenham, 2012
Nelsen arrived at Tottenham shortly after Redknapp had agreed to sign Louis Saha in a free transfer from Everton. The striker had endured a number of fitness problems at Goodison Park during his four years on Merseyside, and would go on to only play 12 games at Spurs.
Redknapp awarded the Frenchman an 18-month contract to join from the Toffees, but he only saw out the first six. Spurs let the two-time Premier League winner with Manchester United leave after starting just six games. He did manage to score four and assist one goal.
Brad Friedel – Aston Villa to Tottenham, 2011
Brad Friedel left Aston Villa at the end of his contract in 2011 and snubbed possible moves to Liverpool, West Brom or Galatasaray to join Tottenham in a free transfer, The Guardian reported. The goalkeeper would spend four years in north London before retiring in 2015.
Spurs had signed the American to support Heurelho Gomes and Carlo Cudicini under boss Redknapp. Instead, Friedel was the first-choice in his debut season with 38 Premier League appearances. But he would only play a further 29 games and last featured in March 2014.

William Gallas – Arsenal to Tottenham, 2010
William Gallas continued his tour of London sides in 2010 by leaving Arsenal for Tottenham after previously playing for Chelsea. Redknapp jumped at a chance to sign the Frenchman for free, and BBC Sport even reported the defender took a pay cut to leave the Gunners.
Arsenal had also asked Gallas to reduce his pay in a shortened deal to stay at the Emirates Stadium. He had captained the Gunners, as well, before going on to play 78 times for Spurs across all competitions. He also featured in four north London derbies with Tottenham.
Jimmy Walker – West Ham to Tottenham, 2009
Tottenham signed a 36-year-old goalkeeper in the summer of 2009 with a free transfer for Jimmy Walker from West Ham. Redknapp had looked to land a new option after growing dissatisfied with Cudicini’s efforts between the sticks following his arrival earlier that year.
Walker would never feature for Spurs, however, and left at the end of his first season with the club. He also only sat on the bench for a top-flight fixture once, coming on the final day at Burnley. Additionally, Walker only made the bench for two of Spurs’ three EFL Cup ties.

Carlo Cudicini – Chelsea to Tottenham, 2009
Cudicini left Chelsea for Tottenham for free in the January 2009 market aged 35 to provide competition for Gomes as the Brazilian had drawn plenty of criticism for his performances. The Italian is now back at Stamford Bridge working as the loan player manager since 2019.
His Spurs career would feature 37 appearances in all competitions up until leaving in 2013 for MLS franchise LA Galaxy. Cudicini never played more than eight Premier League games in a single season for Spurs, though. He also conceded 39 goals to 12 clean sheets in total.
Cesar Sanchez – Real Zaragoza to Tottenham, 2008
Cesar Sanchez was yet another goalkeeper Tottenham signed in a free transfer after he left Real Zaragoza in 2008. Juande Ramos sought the Spaniard’s signature after pulling the plug on a deal for Derby County shot-stopper Stephen Bywater in his search for Gomes’ backup.
But the one-time international only spent a season at Spurs before returning to Spain with Valencia. He also only played once for Tottenham, with Sanchez making his debut and only outing in a 4-2 League Cup victory over Liverpool following Redknapp’s arrival at the helm.
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