Tottenham Hotspur have featured in every Premier League season since 1992, with the club enjoying plenty of memorable moments but also enduring some difficult periods along the way.
While Spurs have had more than enough quality to build an impressive all-time XI, not every player who pulled on the famous white shirt left a positive mark.
From costly signings to players who simply failed to live up to expectations, FootballWhispers selects Tottenham Hotspur's worst all-time Premier League XI.
Tottenham's worst all-time Premier League XI
Tottenham Hotspur
GK: Heurelho Gomes
Heurelho Gomes arrived at Tottenham with a strong reputation from PSV Eindhoven but quickly became synonymous with costly mistakes and uncertainty between the posts.
His struggles were so pronounced that Alan Hansen once described him as “the worst goalkeeper I have ever seen”, although the Brazilian later enjoyed a respectable Premier League career with Watford.
RB: Emerson Royal
Emerson Royal arrived from Barcelona for around £25m in 2021 but never consistently convinced at right-back during his time in North London.
His attacking output was limited and he struggled to establish himself as an undisputed starter before eventually leaving for AC Milan where he stayed for less than 12 months.
CB: Vlad Chiriches
Chiriches was one of the seven players Tottenham signed with the money generated by Gareth Bale's world-record move to Real Madrid in 2013, arriving from Steaua Bucharest for around £8.5m
He made a promising start, but his form dropped off and he became increasingly peripheral under Mauricio Pochettino, eventually leaving for Napoli after just two seasons and 43 appearances in all competitions.
CB: Federico Fazio
Fazio joined Tottenham from Sevilla in 2014 after helping the Spanish club win the Europa League, but the Argentine struggled to establish himself in Mauricio Pochettino's defence.
He made just 20 Premier League appearances for Spurs before returning to Sevilla on loan and subsequently leaving permanently to Italian side Roma.
LB: DeAndre Yedlin
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Yedlin arrived from Seattle Sounders in 2014 after making his name at the World Cup with the United States, but he never established himself at Tottenham.
While he has played mainly as a right-back during his career, he has featured on the left hand side at times.
The full-back made just one Premier League appearance for Spurs before spending time on loan at Sunderland and eventually joining Newcastle United.
CM: Moussa Sissoko
Sissoko became one of the most frustrating signings of the Mauricio Pochettino era after joining from Newcastle United for around £30m in 2016.
His early Spurs career was plagued by criticism, although he eventually became a more important squad player and reached the Champions League final.
Unfortunately, his most infamous Spurs moment came in that final, when Sadio Mané's cross struck his outstretched arm inside the opening 30 seconds, resulting in a penalty that Mohamed Salah converted.
While it was a harsh decision, it gave Liverpool an early lead in Tottenham's first ever Champions League final.
CM: Gedson Fernandes
Gedson Fernandes joined Tottenham on an 18-month loan from Benfica in January 2020 but struggled to make any meaningful impact.
He made just seven Premier League appearances, never starting a league game for Spurs, before his loan was cut short after 18 months had been planned.
His spell was particularly disappointing given the circumstances around his arrival, with the Portuguese midfielder even looking out of place when Spurs played a famous FA Cup tie against eighth-tier Marine.
CM : Tanguy Ndombele
Ndombele arrived from Lyon in 2019 as Tottenham's club-record signing, with the initial fee reported at £54m and the deal potentially rising further.
He did at least score on his Premier League debut against Aston Villa, but injuries, fitness concerns and questions over his attitude quickly overshadowed his obvious ability.
Jose Mourinho was particularly critical after withdrawing him at half-time against Burnley, saying Ndombele had “had enough time to come to a different level” and that he expected more from a player of his potential.
RW: David Bentley
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Bentley arrived from Blackburn Rovers in 2008 for a reported £15m after establishing himself as one of the Premier League's most promising right-sided players.
He never reproduced that form consistently at Tottenham, making just 42 Premier League appearances and struggling to nail down a regular place.
The winger spent much of his Spurs career either out of favour or on loan before leaving the club in 2013, making him a costly signing who never came close to matching the expectations surrounding his arrival.
He also has the rare, and perhaps unwanted, distinction of having played for both Arsenal and Tottenham.
LW: Georges-Kevin Nkoudou
Nkoudou joined Tottenham from Marseille in 2016 but never managed to establish himself in Mauricio Pochettino's first-team plans.
He made just 11 Premier League appearances for Spurs, scoring once, and spent time on loan at Burnley and Monaco.
The French winger eventually left permanently for Besiktas in 2019, bringing an underwhelming Tottenham spell to an end.
ST: Vincent Janssen
Janssen arrived from AZ Alkmaar in 2016 after finishing as the Eredivisie's top scorer, but the Dutchman struggled badly to translate his goalscoring form to the Premier League.
He scored just twice in 31 league appearances for Tottenham and never looked capable of providing sustained competition for Harry Kane.
His failure was particularly damaging given the £17m fee Spurs paid for him and the expectation that he could provide a genuine alternative up front.