Winks is awaiting a work permit before travelling to Italy to complete a medical and sign a season-long deal with Serie A club Sampdoria, with Spurs understood to be paying a portion of the midfielder’s wages.
Reguilon is set for a medical with Atletico Madrid on Tuesday ahead of a season-long loan move.
Neither deal is understood to include an option to make the move permanent at the end of the season, as Spurs focus on offloading unwanted players by whatever means necessary ahead of Thursday’s deadline.
Winks and Reguilon have both been training alone since the start of pre-season having been left out of Antonio Conte’s plans for the campaign.
Valencia are pushing to re-sign Bryan Gil on loan but Spurs will not release the winger without a replacement. Leeds’ Daniel James has been considered but Spurs’ interest is not thought to be serious at present, while the club have denied talks for Atletico Madrid’s Yannick Carrasco.
On Tuesday morning, Spurs announced they have triggered their option to sign Cristian Romero on a permanent deal worth £46.5million, taking their spending this summer beyond £150million – the figure injected by owners ENIC in May.
Romero was on loan last season but has now agreed a five-year deal until 2027 after establishing himself on the right side of Conte’s back three.
The Argentine international has missed the last two games with an adductor injury but trained yesterday and is expected to be in the squad for tomorrow’s derby against West Ham.