On the back of a fifth-placed finish in the Premier League, head coach Ange Postecoglou is now bidding to freshen up his squad.
Archie Gray is a notable addition from Leeds United, while Swedish youngster Lucas Bergvall and versatile attacker Timo Werner will each be part of the senior ranks for 2024-25.
The latter two will come into consideration for the engine room, an area of the pitch where more incomings and outgoings will likely materialise in due course.
Over the weekend, reports and images on social media showed Pierre-Emile Hojbjerg with Marseille officials ahead of what is being claimed to be a £17m deal.
Generating that fee is a considerable positive for Spurs, yet it may have ramifications for a player such as Skipp, who was behind the Denmark international in the pecking order.
Spurs to contemplate Skipp sale
With 16 of Skipp's 21 Premier League appearances last season coming from the substitutes' bench, it is clear that he is not necessarily in the plans of Postecoglou.
However, according to Football Insider, Spurs have no intention of considering a sale unless they are able to acquire a suitable replacement.
That will be based on meeting certain squad criteria with the 23-year-old counting towards Spurs' academy graduates and a general homegrown talent.
Spurs drop one below the allotted eight players required for the latter should they cash in on Skipp, leaving them requiring an alternative who would fulfil the same regulations.
Leicester City are said to be monitoring the situation with Skipp having allowed Kiernan Dewsbury-Hall to sign for Chelsea in a £30m deal.
What is Skipp's preference?
As someone who has been part of Spurs since 2008, it is unclear whether Skipp's preference is to remain with Spurs or try to kick-start his career elsewhere.
With three years left on his contract, the former England Under-21 international does not necessarily have to be in a rush to decide, and that arguably suits Spurs, too.
Skipp is the only outfield player with a Spurs academy background who is in contention for senior starts, something that the North Londoners naturally want to change in due course.
Dane Scarlett could plausibly be kept as part of the first-team squad for next season, yet scoring just six times across 52 loan appearances for Portsmouth and Ipswich Town suggests that Postecoglou will not hand him many minutes either domestically or in the Europa League.