With the free transfers of Andy Robertson and Marcos Senesi seemingly all but done, there is no better time to look back at all of Tottenham’s free transfers since 1992 and rank them accordingly.This list will count down from the worst to the best in terms of impact, ability, value, and Tottenham Hotspur legacy.Spase Dilevski, Edson Sousa, Lars Hirschfeld, Diego Bortolozzo, Dave Beasant, Jimmy Walker, Cesar Sanchez, Joe Hart and Mark Hughes – not that one – won’t feature as none of them ever made a Premier League appearance for Spurs.22. Hans Segers One game in the Premier League for Tottenham. Not much else to say. 118 for Wimbledon, though. Last place.21. Jonathan BlondelThe Belgian midfielder managed two appearances, doubling Segers’ thus concluding his slightly better position in this list. If we continue to see appearances double from the last player, number 1 will have made 33,554,432 appearances. Unlikely. 20. Roger Nilsen The Norwegian defender joined in the 1998/99 season, failed to make a lasting impact and is largely regarded as an unremarkable, uninspiring brief squad addition to those that can remember him.19. Milenko AcimovicAcimovic was a former Slovenian left midfielder, signed from Red Star on a free; he made 17 appearances in his only season in North London, registering one assist. Forgettable.18. Rohan Ricketts The former Arsenal youth prospect has had a very interesting journeyman career, plying his trade in Bangladesh, Ecuador, India and Thailand to name a few. The London-born winger managed 30 Premier League appearances for Tottenham, registering a goal and an assist.Credit: @shooting.practice on Instagram17. Manor SolomonThe most recent free transfer signing, Solomon has never been able to establish himself as a regular at Tottenham, only making five Premier League appearances before departing on numerous loans. He initially showed promise under Ange Postecoglou but a severe knee injury in October 2023 derailed his debut season.He is still contracted to Tottenham, but it feels increasingly unlikely we will ever see him play in Lilywhite again.16. Fraser Forster The 6″7 giant was a valued addition; he met homegrown quotas and was known for his shot-stopping, size, and reliability in cup matches. While he was occasionally criticised for his distribution and made some big mistakes in big games, he sort of did everything you expect from an older, backup keeper.‘Big Frase’ was part of the Europa League winning squad, so for that, I’ll always love him.15. Carlo Cudicini The first Premier League winner on this list, it’s just a shame he won it wearing blue. Joining on a free transfer from Chelsea in 2009, the Italian’s time at Spurs was defined by professionalism and some crucial cup performances, before suffering a severe motorcycle accident that derailed his career.14. Neil Sullivan Remaining on the theme of backup goalkeepers, the 1999/00 season saw Sullivan join Spurs on a free. Highly regarded by supporters as a dependable shot-stopper, the Englishman competed with Ian Walker for the number one shirt during his stint at White Hart Lane.13. Kasey Keller Signed initially signed as backup to Neil Sullivan, who sits just before him in this list, Keller was seen as a calming, reliable presence in what was a tumultuous time at Tottenham.Not the only American goalkeeper that’ll feature on this list, he was widely praised for being solid and sound.Photo by Vince Mignott/MB Media/Getty Images12. Jamie RedknappRedknapp sits, like so many others, in the ‘what could have been’ category for many fans. A clearly skilled, silky midfielder who added genuine quality to Tottenham, it was always felt like we never got to see him at his best. His coverage of Tottenham as a pundit may make you think otherwise, but there was a time he was genuinely adored in N17.11. Paul Stalteri To many, the former Canada captain is the definition of a reliable fullback: relatively solid, reliable and hardworking. He came in, did his job, scored THAT 94th-minute winner against West Ham and left. He can still be found talking about the club fondly in interviews as well, which is always nice. 10 and 9. Ryan Nelsen and Louis SahaOn January 31st 2012, Deadline Day, Tottenham signed Louis Saha from Everton and Ryan Nelsen from Blackburn, while agreeing to loan Sebastian Bassong to Wolves and sell Roman Pavlyuchenko to Lokomotiv Moscow, in a flurry of late transfer business.Rumours state that the then Tottenham coach campaigned for Luis Suarez and Eden Hazard, but was given these two 30+ year olds as free alternatives in the name of ‘experience’.No one expected them to set the world alight, and this transfer turbulence really summarised Spurs’ transfer ‘struggles’.But the duo did display some individual quality – more Saha than Nelsen – so they deserve a respectable spot on the list.8. Clive WilsonAny free transfer that comes in and immediately earns his spot in the starting eleven deserves a good spot on this list. Signed by his former QPR manager Gerry Francis, the English fullback is remembered fondly by Spurs fans as smart, dependable, and highly capable.Out of everyone on this list, Wilson sits near the top for appearances made for the club, too.7. William GallasBrought in by Redknapp to provide cover for an injury-plagued defence, he quickly proved his worth with composed performances in the league and was an instrumental figure in the 2010/11 Champions League campaign.The Frenchmen’s ability speaks for itself, but you can never trust a man that’s played for Chelsea, Arsenal and Tottenham6. Ivan PerišićIt’s difficult to properly analyse Perišić’s spell at Tottenham; he was a highly experienced squad addition with tons of quality that looked like an amazing coup on paper.But limited by inconsistent form, defensive frailties and having to play in a wing-back system in the most intense league past his physical prime, leaves some with a sour taste when discussing the Croatian.He arguably possessed the best crossing ability we’ve seen for a long time at the club – capable of whipping in dangerous balls and inswinging corners with either foot. He linked up well with Harry Kane, sat down Virgil Van Dijk and for a brief moment summed up everything we thought was growing under Antonio Conte.5. Nicola Berti “Oi, gorgeous, what’s your name?”When the Italian arrived midway through the 1997/98 season, Spurs were in serious danger of going down, but the midfielder galvanised Spurs to midtable safety.You can hear his name ring around the stadium to this day, and whispers of his playboy antics still haunt the high road.It was short, it was sweet, it was straordinario.4. Teemu TainioThis is what you call a real cult hero.He was a boyhood Spurs fan, turned down more money from other teams to play at White Hart Lane, attended games with the paying fans and even worked for the club as their Scandinavian scout. He has one of the best sequences in cup final football where he just refused to take the throw-in, rattling Didier Drogba and Joe Cole in the process. Proper Spurs.3. Brad Friedel The oldest player to play for this club, Brad Friedel, was a quality free transfer. Signed in 2011 at the age of 40, the American played every single Premier League match in 2011/12 and was instrumental in helping Spurs finish fourth.He extended his legendary Premier League record for consecutive appearances to 310 games and served as a valuable mentor and a trusted backup until his retirement in 2015 at the age of 44.2. Edgar Davids The Dutch icon is without a doubt the highest level of footballer that Spurs have ever signed on a free. Joining in 2005 from Inter Milan, the 32-year-old brought much-needed aggression and leadership to a young, developing squad and quickly became a fan favourite, helping Spurs shed their ‘soft’ reputation.While he was past the physical peak of his illustrious career, his technical ability was still on show for 18 exciting months, as he demonstrated that he was still a world-class operator. ‘The Pitbull’ was instrumental in moving Spurs into a new cultural era, mentoring youngsters and clattering anyone else who got in his way.Credit: @AlfieNicholsonJournalism1. Teddy Sheringham Some people are just born to play for Spurs, so It was heartbreak around The Lane when Teddy moved to Manchester. The Spurs legend would go on to win everything at United before a second spell at the turn of the century provided a second chapter in his Tottenham tale. Returning as the reigning PFA and Football Writers’ Player of the Year, the English forward would spend two more seasons, scoring another 26 goals in 80 appearances across competitions.In his first season back, Teddy spearheaded Spurs to a ninth-place finish – the highest in six years – while also reaching the League Cup final. Whilst naturally more impressive in his first stint as a younger man at Spurs, the eventual return felt warm and filled the stands with hope.Sheringham is undoubtedly a Premier League great, and a Tottenham legend.The post Ranking every free Tottenham transfer in the Premier League era from 22nd to 1st appeared first on Spurs Web.