Tottenham’s worst Premier League signings of all time

Tottenham Hotspur have featured in every Premier League season since the competition was formed in 1992, experiencing some remarkable highs and painful lows along the way.

The North London club have come agonisingly close to winning the title, while also suffering back-to-back 17th-placed finishes and only securing their top-flight status on the final day in May.

Some of those inconsistencies can be traced back to expensive signings who failed to live up to their price tags or make the expected impact at Spurs.

Spurs have also endured periods of remarkable inactivity in the transfer market, going a world-record 517 days without signing a first-team player between Lucas Moura's arrival in January 2018 and Jack Clarke's move in July 2019.

While the club have made some outstanding additions over the years, including Dele for just £5m and Europa League-winning captain Son Heung-min, there have also been plenty of transfers that failed for a variety of reasons.

Here, Football Whispers counts down five of Tottenham Hotspur's worst signings of the Premier League era.

5) Tanguy Ndombele

After finishing the 2018-19 season as Champions League runners-up, the logical next step for Tottenham was to invest in world-class players who could help the North London side go one step further.

Spurs fans certainly cannot accuse the club of failing to spend, with Tanguy Ndombele arriving from Lyon for a then-club-record £55.5 million fee.

The French midfielder scored on his debut against Aston Villa, but recurring fitness problems and concerns over his work rate quickly overshadowed his promising start. His relationship with several managers deteriorated, while his inability to consistently play beyond the hour mark became a growing frustration for supporters.

Ndombele was famously substituted at half-time against Burnley in 2020, with Jose Mourinho subsequently questioning his effort and intensity.

He made 63 Premier League appearances for Tottenham before leaving on a series of loan spells, eventually waving goodbye to his reported £200,000-a-week contract when he departed permanently for Nice in 2024.

The first name on our list is entering the new campaign without a club, aged just 29.

4) Vincent Janssen

Vincent Janssen's move to North London created plenty of excitement, with the highly rated Dutch forward arriving from AZ Alkmaar with a reputation as a serious goalscoring threat.

He signed for Mauricio Pochettino's side in 2016 for around £17 million, but struggled to make an impact at Spurs, making just 31 Premier League appearances across three seasons and scoring only twice.

With Harry Kane and Son Heung-min ahead of him in the pecking order, Janssen found opportunities difficult to come by, even when the pair were unavailable.

At one stage, he had registered 33 shots in all competitions without scoring, excluding penalties, the most of any Premier League striker at the time.

The Dutchman eventually left Tottenham permanently for Mexican club Monterrey, where he spent three seasons before returning to Europe with Antwerp.

After rediscovering some of his goalscoring form in Belgium, Janssen moved to MLS side Portland Timbers.

3) Paulinho

When Gareth Bale departed Tottenham for Real Madrid in the summer of 2013 for a then-world-record transfer fee, there were high hopes that the money would be reinvested wisely and help the club take another step forward.

Sadly, that was not the case, with the majority of the £85m spent on players who failed to live up to expectations, including Brazilian midfielder Paulinho.

A box-to-box midfielder, Paulinho arrived on the back of several impressive displays for Brazil but ultimately proved to be a major disappointment after struggling to adapt to the Premier League and falling out of favour after just 18 months.

Paulinho made 45 Premier League appearances across two campaigns before sealing a move to Chinese side Guangzhou Evergrande and then, somewhat surprisingly, joining Barcelona in 2017.

On September 8, 2024, Paulinho announced his retirement from professional football after making more than 650 career appearances, clearly finding his feet at everywhere but Tottenham Hotspur.

2) Roberto Soldado

Roberto Soldado was another of the ‘Bale Money’ arrivals who came to N17 with huge expectations and the hope of leading the line for Tottenham for years to come. However, like Paulinho, he ultimately became one of those signings Spurs fans wish had never happened.

Signed in 2013, the Spanish striker arrived at Tottenham for a sizeable £26m fee after several successful seasons in LaLiga, where he had consistently impressed for the likes of Getafe and Valencia.

His final season with Los Che saw him score 24 goals in 35 games, more goal involvements than he managed across two seasons at White Hart Lane.

Soldado scored a winner on his debut but never really produced anything like it again, eventually ending his Spurs career with 16 goals in 76 appearances across all competitions.

Thankfully for the North London side, he departed just as Harry Kane had completed his first full campaign as Tottenham’s main forward, with the English striker netting 21 goals in 34 Premier League matches and fixing their striker woes for free.

The Spaniard had arrived in North London having scored in double figures in six consecutive seasons, but he never reached that mark again during the remainder of his career.

1) Gedson Fernandes

The only player on this list who never signed on a permanent basis but still takes the top spot is Gedson Fernandes.

The Portuguese midfielder joined Tottenham on an 18-month loan deal from Benfica, although his spell was cut short by six months.

He made just seven Premier League appearances during his time at Tottenham Hotspur Stadium and never managed to establish himself in the first team.

After being left out of Tottenham’s Europa League squad, he was included in the XI that faced eighth-tier Marine in the famous FA Cup clash, where he still struggled to make an impact.

In the multiple transfer windows surrounding his arrival, Spurs had also agreed a deal with Sporting Lisbon midfielder Bruno Fernandes.

The Portuguese midfielder famously waved goodbye to Sporting fans in tears, expecting to complete a move to Tottenham in the following days, only for the transfer to fall through before he eventually joined Manchester United.

Unfortunately for Spurs fans, they ended up with the wrong Fernandes.

Gedson left Tottenham having never started a Premier League match or produced a performance of real note, with the midfielder now playing for Spartak Moscow.