Why Spurs may now regret Luton Town transfer decision - is Jack Wilshere laughing? | OneFootball

Tottenham made a seven-figure sale in the summer, but could they be regretting that now, given their recent struggles in all competitions?

It's fair to say that barely any football fan would have predicted the demise of Tottenham Hotspur this season, and that would include rivals fans with a biased opinion on Spurs.

Spurs find themselves 16th in the Premier League table, and just a single point above the relegation zone, which will have the club's supporters fearing an unthinkable relegation into the Championship.

Injuries have certainly played their part in Tottenham's struggles this term, but they've certainly not helped themselves with some of the performances from certain individuals in the 2025/26 league campaign.

Most notably, the goalkeeping performances from Guglielmo Vicario have come under scrutiny in recent months, with the 29-year-old shot-stopper making some notable errors, which have ultimately cost Spurs crucial points, which would have been useful in the battle to avoid relegation into the second tier.

Despite Spurs having enough depth in their goalkeeping options, they simply aren't performing to the required standard at this moment in time. This means that they could potentially be regretting Josh Keeley's depature from the club in July 2025 for a rumoured fee of £1million to League One club, Luton Town.

Spurs could have regret over Keeley deal

Keeley didn't make a single first-team appearance for Tottenham in his time with the club, in a spell which lasted three years, after the goalkeeper originally signed from Irish side St Patrick's Athletic.

The 22-year-old had loan spells with the likes of Barnet and Leyton Orient, before making the permanent switch to Kenilworth Road with Luton Town, who will be looking to force themselves into the play-offs in League One before this year's campaign reaches a conclusion.

Keeley has gone on to make 37 appearances in all competitions for the Hatters, and is Jack Wilshere's first-choice goalkeeper between the posts.

He's caught the eye with some strong showings as well, which includes in a 1-1 draw with Doncaster Rovers, which was then followed by a 2-1 win over promotion-chasing Wycombe Wanderers, where Keeley achieved a SofaScore rating of 7.1.

Kinský's disastrous showing

Plenty of Tottenham supporters were pleased to see Antonín Kinský given an opportunity to impress for Spurs in the first-leg of their Champions League clash with Atletico Madrid, especially given some of the poor performances from Guglielmo Vicario lately.

However, it couldn't have gone much worse for Kinský, as he conceded three goals in the space of a chaotic opening 15 minutes in Spain. One of those was a blatant error from the Czech Republic youth international, and he was substituted shortly after, which sparked plenty of debate from fans of Spurs and other clubs.

It's safe to say that Kinský will have to do something spectacular to work his way back into Igor Tudor's plans moving forward, and Spurs could potentially be regretting letting Josh Keeley leave the club for a minimal fee before this year's campaign started.

The Irishman still has age on his side at 22, and given Spurs' recent struggles in goal and defensively, the Premier League side certainly could have benefitted from having a player of his potential in their squad.

Keeley Vs. Vicaro - Statistical breakdown

The two goalkeepers are relatively close in most statistics, and, of course, it's worth remembering the different levels at which both of these goalkeepers are playing at.

Statistics shown in table are obtained from SofaScore, and are correct as of 17/03/26. Statistics are subject to change.

Vicario has certainly been the busier of the two goalkeepers, and that's shown by the amount of saves per game being more than Keeley's, which isn't too surprising, especially considering that Luton Town have shown promising signs in some matches, where they've dominated the possession.

Keeley has kept four more clean sheets than Vicario though, and it does beg the question as to whether Spurs will have transfer regret over letting Keeley go for a relatively small transfer fee.

Spurs' loss is Luton's gain on this front though, and if Keeley can continue to build on his strong performances for the Hatters, then Jack Wilshere will almost certainly have the last laugh, especially if Spurs are to be relegated from the Premier League this term.