According to reports from The Sunday People, new Spurs manager Mauricio Pochettino looks set to swoop for Bertrand - a player he first targeted during his previous stint as Southampton boss - with Danny Rose currently the club's only real natural and established left-back option.
Rose broke into Tottenham's first-team on a regular basis during 2013/14 after impressing during a prosperous loan stint at Sunderland, yet largely failed to convince many supporters that he was the ideal man to fill the void at White Hart Lane.
Bertrand, meanwhile, had looked surplus to requirements at Chelsea since the return of Jose Mourinho, with the England international having spent the latter half of the season helping Aston Villa avoid relegation to the Championship.
While has has occupied the role as understudy to compatriot Ashley Cole at Stamford Bridge for many years now, the elevation of Cesar Azpilicueta - ordinarily a right-back - to first choice on the left-hand side and the club's reported pursuit of Atletico Madrid defender Filipe Luis would seem to suggest that Bertrand does not feature prominently in Mourinho's plans for the future.
News of Tottenham's apparent interest in Bertrand could cause Liverpool some concern, with the Reds linked with a summer move for the 24-year-old ahead of their return to the Champions League.
Jose Enrique's torrid recent spell with injury - coupled the unimpressive form displayed by former loanee Aly Cissokho - has left Brendan Rodgers somewhat short of options at left-back, with Liverpool fans obviously concerned over a general lack of defensive solidity following a slightly wobbly end to an otherwise fantastic season at Anfield.
Rodgers will presumably be hoping that his previous experience with £6 million-rated Bertrand - he worked with him both in two previous roles as a coach at Chelsea and manager at Championship outfit Reading - will be enough to entice him to Liverpool.