Tottenham fans name their top ten most horrific signings of all time, and one still plays for the club

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Tottenham Hotspur fans have sparked debate after listing the club’s most disastrous transfer deals, with some familiar names featuring heavily among their top ten.

When it comes to signing players during transfer windows, it is often hit or miss, as certain players thrive while others flop.

Tottenham Hotspur have had their fair share of these in recent windows, as the club has spent well over a billion pounds in the last two decades signing players, but not everyone has been a success.

Tottenham fans have now named ten players they believe have been horrific signings throughout the club’s history.

Tottenham Fans Supporters

Credit: @thefrederikkejensen / Instagram

Tottenham supporters debate their worst signings of all time

Taking to X, when asked who the most horrific signings have been for the club, several fans replied with their choice picks.

One fan said: “Ndombele, without a doubt.” Another stated: “Vlad Chiriches, do not care the fee, he was horrible to watch.” One more commented: “Darren Bent.”

Another fan opined: “Moussa Sissoko. Ndombele was a bigger bust financially, but we actually paid £30 million for Sissoko and, for whatever reason, played him frequently. That does not even count his penalty early in the Champions League final that doomed us.”

Another added: “Timo Werner x2.” One more replied: “Bryan Gil because not scoring a single goal in four years while costing £21.5 million (€25 million) plus Erik Lamela is crazy.”

More comments kept coming in, with one Tottenham fan saying: “Vincent Janssen has to be up there.” Another added: “Richarlison. He has done more damage being on the pitch for us than Ndombele did never turning up.”

One more wrote: “Gedson Fernandes.” Another stated: “Darren Anderton, talented player but always injured and then suddenly becomes fit enough to play at World Cups and Euros.”

Spurs transfer hits and misses under Thomas Frank

Ahead of the 2025/26 season, Tottenham once more looked to make a few signings and completed six.

Xavi Simons, Kevin Danso, Mathys Tel, Mohammed Kudus, Joao Palhinha and Takai are the players Tottenham brought in as they looked to compete on multiple fronts.

So far, there have been hits with Kudus and Palhinha looking very solid. Danso has proven to be a good squad option, while Takai is yet to feature for Tottenham.

Simons and Tel, however, have been very underwhelming, with the former managing just one assist in his twelve appearances, and if he does not turn his performances around soon, he could well join that list of horrific signings, having cost Tottenham £51 million.

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