The 23-year-old was once heralded as one of the most exciting prospects to emerge from the Lilywhites' academy and has made 106 appearances for the first team since coming through the youth ranks.
Skipp has scored one goal and set up two more for the Lilywhites in that time, rising to prominence under Antonio Conte after initially making his breakthrough under Mauricio Pochettino and Jose Mourinho.
However, the former England Under-21 international had always struggled to cement a regular place in the side, and his fortunes did not change when Ange Postecoglou took charge last summer.
Despite still being under contract for another three years, having penned a long-term extension in 2022, a summer transfer was always expected to come to fruition for Skipp due to his lack of starts.
Skipp 'to undergo Leicester medical on Sunday'
According to The Athletic, the midfielder is now on the cusp of joining newly-promoted Leicester, who will pay a fee in excess of £20m to add Skipp to Steve Cooper's ranks.
The 23-year-old is expected to undergo his medical with the Foxes on Sunday, one day before they square off with Tottenham in their opening Premier League game at the King Power Stadium.
All parties apparently believe that the deal is a win-win, as Tottenham are making pure profit on an out-of-favour midfielder who should immediately slot into Cooper's Leicester system.
Skipp's move to the King Power will see him reunite with ex-Spurs teammate Harry Winks, who also left the Tottenham Hotspur Stadium for Leicester last year and played a key role in their Championship title win.
The 23-year-old could also fill the void left by Kiernan Dewsbury-Hall's move to Chelsea, and he departs Tottenham after 16 years of service, having joined their youth academy from Manchester City in 2008.
Before becoming a fully-fledged member of the Tottenham squad, Skipp also enjoyed a worthwhile loan spell at Norwich City in the 2020-21 season, helping the Canaries win promotion to the top flight.
Postecoglou clearout continues as Skipp to become 13th exit
Considering Skipp's extreme lack of starts last season - five in the Premier League to be exact - £20m is an especially good deal on Tottenham's side, as Postecoglou continues to trim his squad to his vision.
The midfielder will become the 13th player to leave Tottenham either on loan or permanently this summer, but only the fourth to leave for a fee after Troy Parrott, Emerson Royal and Joe Rodon.
Eric Dier, Ivan Perisic, Japhet Tanganga, Ryan Sessegnon and Tanguy Ndombele were all allowed to head elsewhere for free, while Dane Scarlett, Bryan Gil, Pierre-Emile Hojbjerg and Alejo Veliz have been loaned out.
More departures before the August 30 deadline cannot be ruled out, as Richarlison, Giovani Lo Celso, Manor Solomon and Sergio Reguilon are all facing uncertain futures in North London.