January 30, 2024

Spurs have conducted some excellent business in the January transfer window over the years, signing the likes of Dele Alli, Lucas Moura, Rodrigo Bentancur and Dejan Kulusevski to name a few.


However, the Lilywhites have had their fair share of questionable transfers, some of which simply make you wonder, ‘What on earth were we thinking?’


So, with this year’s January transfer window coming to a close, who are the worst January signings in Tottenham history? We’ve compiled a list ranking the top 10, factoring in price, stats, ability, and ROI (return on investment). Brace yourself for this trip down memory lane, it’s not pretty.


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10. Lewis Holtby (2013)

The German midfielder signed for Spurs from Schalke 04 in 2013 for a fee of £1.5 million. After an impressive start to his final season with the German club, Spurs fast-tracked the move following an initial pre-contract agreement for the summer.


With this decision came an added weight of excitement and expectation for the young German player, however, he failed to hit the ground running with little, if any, impact during his short spell at the club.


Despite being adored by some fans, myself included, for his bubbly personality and strong work ethic, the German only featured 39 times for Spurs, scoring just twice [via Transfermarkt]. Holtby was loaned to Fulham after his first season with the club, before returning to Germany in 2015.

9. Zeki Fryers (2013)

Signed fom Standard Liège in 2013 for £3 million, Spurs fans were excited by the arrival of Zeki Fyers, a young prospect who had come up through the famous Manchester United academy.


Things certainly didn’t work out as planned though, with the young Englishmen featuring just 15 times for the club’s first team and 23 times for the U23s. Just one year after signing for the Lilywhites, he was sold to Crystal Palace where he went on to feature just 9 times during a three-year spell [via Transfermarkt].


8. Kazyuki Toda (2003)

Following a successful campaign with Japan in the 2022 World Cup, which saw the nation top their group, Spurs thought they had come across a gem by signing the midfielder on loan from Japanese club Shimizu S-Pulse, but this couldn’t be further from the truth.


The Japanese international featured just four times for Spurs [via Transfermarkt] before being sent back to his parent club, proving that judging players off the back of an international tournament is often unrewarding.


7. Steven Pienaar (2011)

When Tottenham signed Steven Pienaar for £3 million in 2011, they were expecting an experienced Premier League midfielder to come in and add value to the squad ahead of a push for European football.


Unfortunately, the South African couldn’t hit the highs he had at Everton, featuring just 18 times for Spurs scoring once and assisting twice [via Transfermarkt]. Pienaar returned to Everton after one season at The Lane.


6. Ryan Nelson (2012)

With Sébastien Bassong joining Wolves in the 2012 January window, Tottenham were on the hunt for a replacement centre-back. Following rumours linking Spurs to some of the most exciting young defenders in Europe, the club had ultimately settled on 35-year-old Ryan Nelsen, who joined on a free transfer from Blackburn Rovers. It’s safe to say that Ryan’s time was underwhelming, featuring just 8 times for the club [via Transfermarkt] before being released in May, only a few months after signing for the club.


5. Hossam Ghaly (2006)


The Egyptian midfielder joined the club for a fee of £2.5 million and is often remembered by Spurs fans for his moment of madness in a game against Blackburn in 2007. Brought on after 29 minutes, Martin Jol had taken Hossam off half an hour later, which saw the midfielder unleash his frustration. This involved removing his shirt, throwing it onto the ground and storming down the tunnel into the dressing room.


This happened to be Hossam’s last game for the club following 34 appearances in two years [via Transfermarkt], before a loan spell to Derby in 2008 ahead of a permanent move away to Al Nassr in 2009.


4. Gedson Fernandes (2020)

Gedson joined the club on an initial 18-month loan deal in 2020, with an option for the deal to be made permanent for a mind-boggling fee of £42.76 million [via Sky Sports]. A fee of such magnitude, one would expect an elite talent, however, Gedson was far from this.


With just 14 appearances across all competitions for Tottenham over a 12-month period [via Transfermarkt], Gedson Fernandes failed to highlight his value and never lived up to his ginormous price tag. The young midfielder was recalled by Benfica within 12 months and now plays in Turkey for Besiktas.


3. Gilberto (2008)

Gilberto joined the club for a fee of £2.5 million in the 2008 January window, the same window in which Alan Hutton and Jonathan Woodgate also arrived at the club. After an impressive spell at Hertha Berlin, netting 15 goals and 16 assists over a four-year spell, there was excitement surrounding the Brazilians’ arrival in Tottenham.


Unfortunately, Gilberto never lived up to the hype, making just 10 appearances for the club in the 2008/9 season [via Transfermarkt], before leaving on a free transfer and returning to Brazil with Cruzeiro.


2. Ricardo Rocha (2007)

It cost Tottenham £3 million to bring in the Portuguese centre-back, who joined the club in 2007 from Benfica. The start to Ricardo’s Spurs career looked promising, regularly appearing in games for the remainder of the 2006/7 season, however, things took a turn with the start of the 2007/8 season.


Ricardo Rocha fell out of favour, with his last appearance for the club in September 2007 – he would stay at the club for another two seasons, not featuring once, before departing the club on a free transfer in 2009. Ricardo made just 14 appearances for Tottenham during a three-year spell at the club [via Transfermarkt].


1. Bongani Khumalo (2011)

Most Spurs fans have probably never heard of Bongani Khumalo, and that’s because his transfer was a complete failure. Bongani joined the club from South African side SuperSport for just over £1 million, his first move outside his native country.


Khumalo would go on to have a five-year spell at the club, from 2011-2015, with zero appearances for the first team – he was loaned out on five separate occasions before re-joining SuperSport in 2016.

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