The January transfer window has been one of frustration for those associated with Tottenham. The north London club has attempted to strengthen their squad, but have been met with obstacles on several potential new signings.

The biggest blow is that of Liverpool beating them to the signing of exciting Colombian international Luis Diaz. The Porto star is reported to have agreed on a move that will cost Liverpool an initial £45million plus £15million in add-ons. Considering the potential of Diaz, that looks like a masterstroke from Liverpool.

Daniel Levy unhappy with Liverpool

It seemed as though Diaz was heading to Tottenham before Liverpool made their move. However, Liverpool swooping in to sign the winger from under Spurs noses has not gone down well with Tottenham chairman Daniel Levy.

Levy was understandably furious that the men from Merseyside had hijacked the deal for their highly-rated target. He threatened to report the club’s recruitment team to Liverpool’s owners the Fenway Group. However, unfortunately for Levy and Spurs, Fenway owners John W Henry and Mike Gordon were impressed by the way that their staff handled the business.

Reportedly, Spurs have also been snubbed in moves for Milan central midfielder Frack Kessie, whose contract with the Rossoneri expires next summer. They also saw another target Adama Traore decide to return to Barcelona rather than join them.

However, the most embarrassing snub came from non-league winger Ollie Tanner. Spurs had agreed on a fee with Lewes for the 19-year-old’s services. However, the club from north London could not agree on personal terms with the youngster.

Still working on deals

Despite the failure to complete the above deals, Tottenham are still working on other deals. Spurs are in talks with Juventus over the signing of the versatile Swedish forward. The 21-year-old would join on loan with a view to a permanent £40million deal in the summer if Spurs qualify for the Champions League. The youngster has struggled for first-team football with the Bianconeri this season.

Tottenham are also talking to Juventus about signing Uruguayan midfielder Rodrigo Bentancur. Reports from Italy suggest that Aston Villa have already had a bid of around £20million, but Villa wanted to pay £16million upfront and £4million in bonuses. The Turin outfit wants all the money upfront to pursue a deal for Dennis Zakaria of Monchengladbach. However, a sticking point could be the fee, as reportedly Tottenham are only interested in signing the midfielder on loan.

Antonio Conte will get impatient

Tottenham head coach Antonio Conte is without a doubt one of the best in the business at getting results. The Italian does have a reputation for leaving clubs if he does get what he asks for in the transfer market.

The fact that Conte has already stated that his squad isn’t good enough is not a great sign for the Tottenham hierarchy. That is the Italian telling the Spurs hierarchy that they need to strengthen the squad.

The Italian’s patience with the clubs struggles in the transfer market will not last forever. If Spurs cannot strengthen the squad before Monday’s deadline, then Conte could be getting very itchy feet in north London.

Tottenham are still in a decent position in the Premier League table. However, with so much competition for that last Champions League spot, strengthening their squad could only enhance their top-four chances, while placating their very combustible head coach.

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Will Tottenham strengthen their squad before the January transfer window closes?