The ex-Spurs midfielder will be available in January as the MLS season enters its off-season break. In the past, players like Landon Donovan have joined Premier League clubs on loan for three month periods before returning for the start of the new MLS campaign in the Spring.
Dempsey left Spurs to join the Seattle Sounders over the summer, and the report claims Tottenham have the first option to bring him back.
Everton and another of Dempsey's former clubs, Fulham, are thought to be keen to bring him back to England.
He'll consider his options in December before making a decision on his future - the most important factor considering the short window available is likely to be first-team football.
That might be something in short supply at White Hart Lane, with Andre Villas-Boas able to call on a number of talented players in Dempsey's preferred position.
That partly forced the American's exit following just 29 first-team league appearances for the club.
The USA captain could be the subject of a three-way Premier League battle though, with Spurs, Everton and Fulham all looking to strengthen in the winter window.