The Lilywhites are starting to plan for life without current number one Hugo Lloris, who turns 37 this year and is out of contract at the end of next season.
Having come under fire for several high-profile mistakes in the 2022-23 campaign, Lloris - who is currently sidelined with a knee injury - is unlikely to stay at Tottenham beyond 2024, and current backup Fraser Forster is not a long-term solution either.
Antonio Conte also has the inexperienced pairing of Alfie Whiteman and Brandon Austin in his ranks, the former of whom recently signed a new contract with the club until 2025.
However, Whiteman and Austin have just one senior Tottenham appearance between them, with the former making his debut back in November 2020 as a substitute against Ludogorets in the Europa League.
As a result, finding a long-term successor to Lloris is high on Tottenham's transfer agenda, but they have seemingly been rebuffed in their pursuit of one potential solution.
According to Gazzetta dello Sport, director Fabio Paratici made an approach to sign Juventus number one Szczesny, but the former Arsenal man quickly rejected that shock move.
As is the case with Lloris, Szczesny is also due to become a free agent in the summer of 2024, but the Poland international is only focused on achieving success with Juventus before a possible move to MLS later in his career.
Furthermore, Juve can trigger a one-year extension in Szczesny's contract to keep him in Turin until 2025, and manager Massimiliano Allegri has also blocked attempts from foreign clubs to prise him away from Italy.
Despite winning a host of accolades with Juventus and becoming one of the top goalkeepers in Serie A, Szczesny's unlikely arrival at Tottenham would have certainly been met with hostility due to his Arsenal connections.
The 32-year-old played 181 games for the Gunners during an 11-year spell between 2006 and 2017, winning two FA Cups and a Community Shield in North London.
After losing his place in the first team to Petr Cech, Szczesny spent two years on loan at Roma between 2015 and 2017, and he has since kept 81 clean sheets in 201 matches for Juventus.
The Poland international has won seven pieces of silverware in Turin - including three Serie A titles - and he made three appearances at the 2022 World Cup, saving a penalty from Lionel Messi in a group-stage defeat to Argentina.
While a move for Szczesny is seemingly off the cards, Spurs have shortlisted a host of other goalkeepers, including Jan Oblak, Dean Henderson, Giorgi Mamardashvili and another former Arsenal man in Emiliano Martinez.
Brentford's David Raya has also been linked with a move to the Tottenham Hotspur Stadium, and the Spaniard recently hinted that he would be prepared to consider a summer transfer.