The Blues manager was linked with both players - who were also believed to be Manchester United targets - during the summer window, and Punto Pelota reports that he's lining up a double swoop for the pair in January.
Coentrao was heavily linked with United in the final days of the window, with the Premier League champions reportedly failing to conclude an eleventh hour loan bid for the out-of-favour Portuguese international.
Germany international Khedira was also a £34m target for United boss David Moyes, but the Old Trafford hierarchy eventually moved to bring in Marouane Fellaini from Everton to strengthen the club's midfield.
Both players starred under Mourinho at the Bernabeu, and the report - also carried by Le 10 Sport - claims talks could resume between Chelsea and Real Madrid in the coming weeks over a double deal for the duo.
Because Khedira and Coentrao have found their Real Madrid places under threat this season. The €38m signing of Real Sociedad star Asier Illaramendi and the emergence of Luka Modric under new boss Carlo Ancelotti has prompted speculation Khedira could be surplus to requirements.
And Coentrao has long played second fiddle to first-choice Madrid left-back Marcelo.
That could allow Mourinho to return to the Bernabeu to persuade the pair to join his new-look Stamford Bridge set-up.
The Blues manager has already begun moulding the squad, with Oscar preferred to Juan Mata, Samuel Eto'o in to rival Fernando Torres and Kevin De Bruyne, Willian, Andre Schurrle and Eden Hazard each competing for two starting spots out wide.