The 10-cap England international came through the academy system with the North Londoners to eventually make 203 appearances in the first team.
However, despite earning regular game time for Spurs across six seasons, his influence petered out under different managers and the decision was eventually taken to cash in on the player.
On the back of making 20 outings on loan at Sampdoria, the 28-year-old has kick-started his career at Leicester, initially dropping down to the Championship to help the Foxes secure an immediate return to the Premier League.
Winks has since remained a key man under Steve Cooper in the top flight, starting nine of Leicester's 11 such fixtures during 2024-25.
As it stands, the current expectation is that Winks will remain an important cog in the engine room for a club that are ultimately competing to remain in the top flight.
Spurs keen on Winks reunion?
Nevertheless, it appears that Spurs hold a certain level of interest in attempting to regain the services of one of their homegrown players in 2025.
As per Fichajes, Spurs and head coach Ange Postecoglou can see a scenario where Winks could flourish if he returned to the club.
Spurs are already well stocked for central midfielders, there being seven players who could realistically slot into Ange Postecoglou's three-man system in the engine room.
That said, it seems that Winks has been placed on a shortlist of potential options should they wish to strengthen that area in January or next summer.
The report claims that Spurs would be willing to spend as much as €38m (£31.78m) on a player that they sold for a fee in the region of £10m less than 18 months ago.
A deal that would suit all parties?
Although this is a deal that would have been viewed unforeseen at both clubs, it could be a transfer that equally makes sense.
Spurs are currently not blessed with senior homegrown talent in their first-team squad, hindering them from a squad-registration perspective in the short and long term.
While that could change as seasons pass by with Postecoglou handing chances to the likes of Mikey Moore and Will Lankshear, there are benefits to Winks returning to the club.
As for Leicester, generating a substantial profit on Winks would hand their position with the Premier League's Profit and Sustainability regulations a considerable boost and give them extra leeway to strengthen elsewhere.