The 23-year-old has made 77 Premier League appearances for Spurs and scored one goal but has struggled to secure a regular spot under Ange Postecoglou.
Last season, Skipp made just 21 appearances for the Lilywhites in the league, most of which were as a substitute.
Since joining the club, Postecoglou has favoured Yves Bissouma and Pape Sarr as his preferred midfield duo, leaving limited starting opportunities for Skipp to accumulate playing time.
The Englishman was recently linked with a move to Leicester City, who signalled their interest in signing him this summer.
Skipp set for unexpected contract extension
Football Insider report that the Foxes will now have to look elsewhere for a midfield target, as Spurs have engaged in discussion over a new contract with the 23-year-old.
The report adds that initial talks have gone well and there is optimism that an agreement between the player and club could be reached by the end of this week.
Given that Skipp's current deal with the Londoners only expires in 2027, and considering his lack of game time, news of a new deal will likely come as a surprise to many fans.
Additionally, Spurs were believed to be willing to sell the player this summer provided they could find a suitable replacement, but it now appears that the midfielder is set to remain at the club.
It is understood that the Lilywhites may have changed their stance on parting ways with Skipp after Pierre-Emile Hojbjerg departed London for Marseille earlier in the window.
The Englishman has spent his entire career at Tottenham, amassing 106 appearances for the Premier League club across all competitions.
Plenty of transfer business expected over the coming weeks
Spurs have had a relatively slow summer in comparison to some of their Premier League rivals, with only two confirmed new signings made to date.
That includes the acquisitions of Archie Gray from Leeds United for around £35m and Lucas Bergvall from Djurgarden for £8.5m. The Lilywhites also opted to extend Timo Werner's loan deal until January.
However, reports suggest that the club are planning for a late window transfer blitz and have set aside a 'huge' sum of money to bring in more new players.
At the top of their priority list is believed to be a number nine, as Postecoglou's side look to find a long-term replacement for Harry Kane, who departed for the Bundesliga last summer.
The Lillywhites have been rumoured to be considering bids for Sporting Lisbon's Viktor Gyokeres and Brentford striker Ivan Toney.