| 27 Nov 14 | Alex Davey |  ChelseaCHE | → |  Scunthorpe UnitedSCU | Loan |
| 15 Nov 14 | T. Kane Todd Kane | ChelseaCHE | → |  Bristol CityBRC | Loan |
| 01 Sept 14 | M. van Ginkel Marco van Ginkel | ChelseaCHE | → |  AC MilanMIL | Loan |
| 01 Sept 14 | M. van Ginkel Marco van Ginkel | ChelseaCHE | → | AC MilanMIL | Loan |
| 01 Sept 14 | J. Blackman Jamal Blackman | ChelseaCHE | → |  MiddlesbroughMID | Loan |
| 01 Sept 14 | J. Blackman Jamal Blackman | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 01 Sept 14 | N. Chalobah Nathaniel Chalobah | ChelseaCHE | → |  BurnleyBUR | Loan |
| 31 Aug 14 | F. Torres Fernando Torres | ChelseaCHE | → | AC MilanMIL | Loan |
| 31 Aug 14 | F. Torres Fernando Torres | ChelseaCHE | → | AC MilanMIL | Loan |
| 31 Aug 14 | L. Rémy Loïc Rémy |  Queens Park RangersQPR | → | ChelseaCHE | Undisclosed |
| 30 Aug 14 | P. Bamford Patrick Bamford | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 30 Aug 14 | P. Bamford Patrick Bamford | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 26 Aug 14 | George Saville | ChelseaCHE | → |  Wolverhampton WanderersWOL | Undisclosed |
| 26 Aug 14 | George Saville | ChelseaCHE | → | Wolverhampton WanderersWOL | Undisclosed |
| 18 Aug 14 | M. Marin Marko Marin | ChelseaCHE | → |  FiorentinaFIO | Loan |
| 18 Aug 14 | J. McEachran Josh McEachran | ChelseaCHE | → |  VitesseVIT | Loan |
| 18 Aug 14 | J. McEachran Josh McEachran | ChelseaCHE | → | VitesseVIT | Loan |
| 18 Aug 14 | M. Marin Marko Marin | ChelseaCHE | → | FiorentinaFIO | Loan |
| 16 Aug 14 | V. Moses Victor Moses | ChelseaCHE | → |  Stoke CitySTK | Loan |
| 13 Aug 14 | C. Atsu Christian Atsu | ChelseaCHE | → |  EvertonEVE | Loan |
| 06 Aug 14 | K. Omeruo Kenneth Omeruo | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 06 Aug 14 | K. Omeruo Kenneth Omeruo | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 05 Aug 14 | J. Rodríguez Joao Rodríguez | ChelseaCHE | → |  BastiaBAS | Loan |
| 05 Aug 14 | J. Rodríguez Joao Rodríguez | ChelseaCHE | → | BastiaBAS | Loan |
| 04 Aug 14 | O. Romeu Oriol Romeu | ChelseaCHE | → |  VfB StuttgartVFB | Loan |
| 04 Aug 14 | O. Romeu Oriol Romeu | ChelseaCHE | → | VfB StuttgartVFB | Loan |
| 01 Aug 14 | J. Swift John Swift | ChelseaCHE | → |  Rotherham UnitedROT | Loan |
| 01 Aug 14 | J. Swift John Swift | ChelseaCHE | → | Rotherham UnitedROT | Loan |
| 30 Jul 14 | G. Kakuta Gaël Kakuta | ChelseaCHE | → |  Rayo VallecanoRAY | Loan |
| 30 Jul 14 | R. Lukaku Romelu Lukaku | ChelseaCHE | → | EvertonEVE | 28000000 |
| 30 Jul 14 | R. Bertrand Ryan Bertrand | ChelseaCHE | → |  SouthamptonSOU | Loan |
| 30 Jul 14 | G. Kakuta Gaël Kakuta | ChelseaCHE | → | Rayo VallecanoRAY | Loan |
| 25 Jul 14 | D. Drogba Didier Drogba | XXX | → | ChelseaCHE | Free |
| 25 Jul 14 | P. van Aanholt Patrick van Aanholt | ChelseaCHE | → |  SunderlandSUN | Undisclosed |
| 24 Jul 14 | L. Piazon Lucas Piazon | ChelseaCHE | → |  Eintracht FrankfurtSGE | Loan |
| 24 Jul 14 | L. Piazon Lucas Piazon | ChelseaCHE | → | Eintracht FrankfurtSGE | Loan |
| 22 Jul 14 | M. Pasalic Mario Pasalic | ChelseaCHE | → |  ElcheELC | Loan |
| 22 Jul 14 | M. Pasalic Mario Pasalic | ChelseaCHE | → | ElcheELC | Loan |
| 18 Jul 14 | D. Ba Demba Ba | ChelseaCHE | → |  BesiktasBES | 6,000,000 |
| 18 Jul 14 | Filipe Luís |  Atletico MadridATL | → | ChelseaCHE | Undisclosed |
| 18 Jul 14 | Filipe Luís | Atletico MadridATL | → | ChelseaCHE | Undisclosed |
| 15 Jul 14 | D. Costa Diego Costa | Atletico MadridATL | → | ChelseaCHE | Undisclosed |
| 15 Jul 14 | D. Costa Diego Costa | Atletico MadridATL | → | ChelseaCHE | Undisclosed |
| 09 Jul 14 | M. Pasalic Mario Pasalic | HSXHajduk SplitHajduk Split | → | ChelseaCHE | Undisclosed |
| 08 Jul 14 | S. Hutchinson Sam Hutchinson | ChelseaCHE | → |  Sheffield WednesdaySHW | Free |
| 08 Jul 14 | S. Hutchinson Sam Hutchinson | ChelseaCHE | → | Sheffield WednesdaySHW | Free |
| 07 Jul 14 | B. Traoré Bertrand Traoré | ChelseaCHE | → | VitesseVIT | Loan |
| 07 Jul 14 | B. Traoré Bertrand Traoré | ChelseaCHE | → | VitesseVIT | Loan |
| 05 Jul 14 | T. Hazard Thorgan Hazard | ChelseaCHE | → |  Borussia MonchengladbachMON | Loan |
| 05 Jul 14 | T. Hazard Thorgan Hazard | ChelseaCHE | → | Borussia MonchengladbachMON | Loan |
| 01 Jul 14 | T. Kalas Tomás Kalas | ChelseaCHE | → |  FC CologneCOL | Loan |
| 01 Jul 14 | W. Oliveira Wallace Oliveira | ChelseaCHE | → | VitesseVIT | Loan |
| 01 Jul 14 | D. Luiz David Luiz | ChelseaCHE | → |  Paris Saint-Germain PSG | Undisclosed |
| 01 Jul 14 | C. Fàbregas Cesc Fàbregas |  BarcelonaBAR | → | ChelseaCHE | Undisclosed |
| 01 Jul 14 | C. Fàbregas Cesc Fàbregas | BarcelonaBAR | → | ChelseaCHE | Undisclosed |
| 01 Jul 14 | D. Luiz David Luiz | ChelseaCHE | → | Paris Saint-Germain PSG | Undisclosed |
| 01 Jul 14 | W. Oliveira Wallace Oliveira | ChelseaCHE | → | VitesseVIT | Loan |
| 14 Feb 14 | S. Hutchinson Sam Hutchinson | ChelseaCHE | → | Sheffield WednesdaySHW | Loan |
| 14 Feb 14 | S. Hutchinson Sam Hutchinson | ChelseaCHE | → | Sheffield WednesdaySHW | Loan |
| 31 Jan 14 | K. Zouma Kurt Zouma |  Saint-EtienneASSE | → | ChelseaCHE | Undisclosed |
| 31 Jan 14 | K. Zouma Kurt Zouma | ChelseaCHE | → | Saint-EtienneASSE | Loan |
| 31 Jan 14 | G. Kakuta Gaël Kakuta | ChelseaCHE | → |  LazioLAZ | Loan |
| 31 Jan 14 | K. Zouma Kurt Zouma | Saint-EtienneASSE | → | ChelseaCHE | Undisclosed |
| 31 Jan 14 | G. Kakuta Gaël Kakuta | ChelseaCHE | → | LazioLAZ | Loan |
| 31 Jan 14 | K. Zouma Kurt Zouma | ChelseaCHE | → | Saint-EtienneASSE | Loan |
| 29 Jan 14 | M. Delac Matej Delac | ChelseaCHE | → | FSXFK SarajevoFK Sarajevo | Loan |
| 27 Jan 14 | M. Essien Michael Essien | ChelseaCHE | → | AC MilanMIL | Free |
| 27 Jan 14 | M. Essien Michael Essien | ChelseaCHE | → | AC MilanMIL | Free |
| 26 Jan 14 | M. Salah Mohamed Salah |  FC BaselBAS | → | ChelseaCHE | Undisclosed |
| 25 Jan 14 | J. Mata Juan Mata | ChelseaCHE | → |  Manchester UnitedMAN | 37100000 |
| 23 Jan 14 | J. McEachran Josh McEachran | ChelseaCHE | → |  Wigan AthleticWGA | Loan |
| 23 Jan 14 | J. McEachran Josh McEachran | ChelseaCHE | → | Wigan AthleticWGA | Loan |
| 20 Jan 14 | S. Walker Sam Walker | ChelseaCHE | → |  Colchester UnitedCOL | Undisclosed |
| 18 Jan 14 | K. De Bruyne Kevin De Bruyne | ChelseaCHE | → |  VfL WolfsburgWOB | Undisclosed |
| 18 Jan 14 | K. De Bruyne Kevin De Bruyne | ChelseaCHE | → | VfL WolfsburgWOB | Undisclosed |
| 17 Jan 14 | R. Bertrand Ryan Bertrand | ChelseaCHE | → |  Aston VillaAVL | Loan |
| 16 Jan 14 | N. Chalobah Nathaniel Chalobah | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 16 Jan 14 | N. Chalobah Nathaniel Chalobah | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 15 Jan 14 | N. Matic Nemanja Matic |  BenficaBEN | → | ChelseaCHE | 20750000 |
| 07 Jan 14 | K. Omeruo Kenneth Omeruo | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 07 Jan 14 | K. Omeruo Kenneth Omeruo | ChelseaCHE | → | MiddlesbroughMID | Loan |
| 06 Jan 14 | P. Bamford Patrick Bamford | ChelseaCHE | → |  Derby CountyDER | Loan |
| 06 Jan 14 | P. Bamford Patrick Bamford | ChelseaCHE | → | Derby CountyDER | Loan |
| 02 Jan 14 | B. Traoré Bertrand Traoré | ChelseaCHE | → | VitesseVIT | Loan |
| 02 Jan 14 | B. Traoré Bertrand Traoré | ChelseaCHE | → | VitesseVIT | Loan |
| 01 Jan 14 | B. Traoré Bertrand Traoré | AJEAssociation Jeunes Espoirs De Bobo-DioulassoAssociation Jeunes Espoirs De Bobo-Dioulasso | → | ChelseaCHE | Free |