Antonio Conte is plotting his first transfer window as Spurs manager alongside director of football Fabio Paratici and chairman Daniel Levy, as the fight for the top four heats up in the Premier League.
It is thought that a centre-half, wing-backs and a replacement for Tanguy Ndombele could be on the agenda with the chance to compete for a first trophy since the League Cup in 2008.
With the FA Cup and Champions League qualification still left as realistic targets to win for the famously trophy-hungry Conte, this January transfer window could be one of Spurs' most important in years.
There are some real gems out there in Europe's top leagues capable of adding quality to any side and with that in mind, we've put together a list of five players from Serie A that Spurs could target this month.
Joakim Mæhle (Atalanta)
Spurs are reportedly on the hunt for a wing-back and Danish international Joakim Mæhle appears to fit the bill nicely, being able to operate on either wing.
The 24-year-old plays on both flanks for club side Atalanta but is primarily left-sided for his national side Denmark, whom he helped reach the semi-finals.
At the tournament it became a familiar sight for Mæhle to cut in on his right-foot and deliver crosses as well as finding space to score - he has scored seven goals in total for Denmark since the beginning of Euros.
Conte will be satisfied that Mæhle's capacity to fit into a three at the back system, having done so for both his club and country as well as being able to play as a wide centre-back in a back three.
His good injury record will also appeal, however his contract runs until 2025 in Bergamo meaning that any deal will be an expensive one for Spurs.
Franck Kessie (AC Milan)
With the future of Tanguy Ndombele increasingly uncertain, Spurs will be looking for a long-term partner for Pierre Emile Højbjerg and Franck Kessie is a prime candidate for this role.
The 25-year-old's contract is up in the summer, meaning that Spurs and other clubs are free to approach the player now for a potential deal.
He has Champions League experience this season with Milan, who currently sit second in Serie A behind arch-rivals Inter and is accustomed to playing in a midfield two.
He is defensively strong while being good on the ball, offering the all-round package as a press resistant, dynamic and composed modern midfielder.
Fabián Ruiz (Napoli)
Another player who would complement Højbjerg is Fabian Ruiz of Napoli, the 25-year-old is out of contract at Diego Armando Maradona in 2023, at the end of next season meaning that the Neopolitans will be keen to cash in.
He is left-footed and would offer ball progression skills similar to Ndombele's that would work well with Højbjerg's defensive solidity and passing game.
He has started at least 29 games in three of the past four seasons, meaning that injuries are unlikely to be a problem with the signing of a player who has gained Champions League experience in his time in Italy.
Spanish international Ruiz has also scored 16 non-penalty goals and registered 13 assists across four seasons in Serie A from midfield and ranks high against his midfield peers for progressive passes and carries.
Milan Skriniar (Inter Milan)
Another area that Conte will be looking to improve is centre-back, having been an area of vulnerability since the departure of Belgian duo Jan Vertonghen and Toby Alderweireld.
Milan Skriniar could be the answer to these woes and will have one year remaining on his contract this summer, with his deal at Inter expiring at the end of the 2022/23 season.
Most promisingly, he is a Serie A title winner, having won the Scudetto under Antonio Conte for two seasons at Inter in his back three system meaning that any transfer would require very little transition.
He has been consistently linked with Spurs in the past and should excite supporters as an impressive distributor of the ball who could bring a winning mentality to a club in need of characters.
