| 20 Sept 13 | J. McEachran Josh McEachran |  ChelseaCHE | → |  WatfordWAT | Loan |
| 20 Sept 13 | J. McEachran Josh McEachran | ChelseaCHE | → | WatfordWAT | Loan |
| 19 Sept 13 | N. Chalobah Nathaniel Chalobah | ChelseaCHE | → |  Nottingham ForestFOR | Loan |
| 19 Sept 13 | N. Chalobah Nathaniel Chalobah | ChelseaCHE | → | Nottingham ForestFOR | Loan |
| 02 Sept 13 | S. Hutchinson Sam Hutchinson | ChelseaCHE | → |  VitesseVIT | Loan |
| 02 Sept 13 | S. Hutchinson Sam Hutchinson | ChelseaCHE | → | VitesseVIT | Loan |
| 02 Sept 13 | R. Lukaku Romelu Lukaku | ChelseaCHE | → |  EvertonEVE | Loan |
| 02 Sept 13 | V. Moses Victor Moses | ChelseaCHE | → |  LiverpoolLIV | Loan |
| 01 Sept 13 | C. Atsu Christian Atsu |  FC PortoPOR | → | ChelseaCHE | Undisclosed |
| 01 Sept 13 | C. Atsu Christian Atsu | ChelseaCHE | → | VitesseVIT | Loan |
| 01 Sept 13 | C. Atsu Christian Atsu | ChelseaCHE | → | VitesseVIT | Loan |
| 29 Aug 13 | S. Eto'o Samuel Eto'o |  Anzhi MakhachkalaANZ | → | ChelseaCHE | Undisclosed |
| 28 Aug 13 | Willian | Anzhi MakhachkalaANZ | → | ChelseaCHE | Undisclosed |
| 19 Aug 13 | Stipe Perica | ChelseaCHE | → |  NAC BredaNAC | Loan |
| 19 Aug 13 | Stipe Perica | ChelseaCHE | → | NAC BredaNAC | Loan |
| 13 Aug 13 | W. Oliveira Wallace Oliveira | ChelseaCHE | → |  InternazionaleINT | Loan |
| 13 Aug 13 | W. Oliveira Wallace Oliveira | ChelseaCHE | → | InternazionaleINT | Loan |
| 09 Aug 13 | L. Piazon Lucas Piazon | ChelseaCHE | → | VitesseVIT | Loan |
| 09 Aug 13 | L. Piazon Lucas Piazon | ChelseaCHE | → | VitesseVIT | Loan |
| 07 Aug 13 | C. Cuevas Cristian Cuevas | ChelseaCHE | → | VitesseVIT | Loan |
| 07 Aug 13 | C. Cuevas Cristian Cuevas | ChelseaCHE | → | VitesseVIT | Loan |
| 23 Jul 13 | C. Cuevas Cristian Cuevas |  O'HigginsOHI | → | ChelseaCHE | Undisclosed |
| 19 Jul 13 | S. Walker Sam Walker | ChelseaCHE | → |  Colchester UnitedCOL | Loan |
| 16 Jul 13 | M. Lalkovic Milan Lalkovic | ChelseaCHE | → |  WalsallWAL | Loan |
| 16 Jul 13 | Daniel Pappoe | ChelseaCHE | → | Colchester UnitedCOL | Loan |
| 13 Jul 13 | J. Bruma Jeffrey Bruma | ChelseaCHE | → |  PSV EindhovenPSV | Undisclosed |
| 13 Jul 13 | J. Bruma Jeffrey Bruma | ChelseaCHE | → | PSV EindhovenPSV | Undisclosed |
| 12 Jul 13 | O. Romeu Oriol Romeu | ChelseaCHE | → |  ValenciaVAL | Loan |
| 12 Jul 13 | O. Romeu Oriol Romeu | ChelseaCHE | → | ValenciaVAL | Loan |
| 10 Jul 13 | B. Clifford Billy Clifford | ChelseaCHE | → |  Yeovil TownYEO | Loan |
| 10 Jul 13 | B. Clifford Billy Clifford | ChelseaCHE | → | Yeovil TownYEO | Loan |
| 09 Jul 13 | M. Schwarzer Mark Schwarzer |  FulhamFUL | → | ChelseaCHE | Free |
| 07 Jul 13 | P. van Aanholt Patrick van Aanholt | ChelseaCHE | → | VitesseVIT | Loan |
| 07 Jul 13 | P. van Aanholt Patrick van Aanholt | ChelseaCHE | → | VitesseVIT | Loan |
| 05 Jul 13 | M. van Ginkel Marco van Ginkel | VitesseVIT | → | ChelseaCHE | Undisclosed |
| 05 Jul 13 | M. van Ginkel Marco van Ginkel | VitesseVIT | → | ChelseaCHE | Undisclosed |
| 01 Jul 13 | T. Kane Todd Kane | ChelseaCHE | → |  Blackburn RoversBLK | Loan |
| 01 Jul 13 | T. Courtois Thibaut Courtois | ChelseaCHE | → |  Atletico MadridATL | Loan |
| 01 Jul 13 | P. Bamford Patrick Bamford | ChelseaCHE | → |  Milton Keynes DonsMKD | Loan |
| 01 Jul 13 | A. Schürrle André Schürrle |  Bayer LeverkusenLEV | → | ChelseaCHE | Undisclosed |
| 01 Jul 13 | M. Marin Marko Marin | ChelseaCHE | → |  SevillaSEV | Loan |
| 01 Jul 13 | G. Saville George Saville | ChelseaCHE | → |  BrentfordBRE | Loan |
| 01 Jul 13 | A. Schürrle André Schürrle | Bayer LeverkusenLEV | → | ChelseaCHE | Undisclosed |
| 01 Jul 13 | M. Marin Marko Marin | ChelseaCHE | → | SevillaSEV | Loan |
| 01 Jul 13 | T. Kane Todd Kane | ChelseaCHE | → | Blackburn RoversBLK | Loan |
| 01 Jul 13 | T. Courtois Thibaut Courtois | ChelseaCHE | → | Atletico MadridATL | Loan |
| 25 Jun 13 | T. Kane Todd Kane | ChelseaCHE | → | Blackburn RoversBLK | Loan |
| 25 Jun 13 | T. Kane Todd Kane | ChelseaCHE | → | Blackburn RoversBLK | Loan |
| 15 Mar 13 | T. Kane Todd Kane | ChelseaCHE | → | Blackburn RoversBLK | Loan |
| 15 Mar 13 | T. Kane Todd Kane | ChelseaCHE | → | Blackburn RoversBLK | Loan |
| 28 Feb 13 | G. Saville George Saville | ChelseaCHE | → |  MillwallMIL | Loan |
| 28 Feb 13 | G. Saville George Saville | ChelseaCHE | → | MillwallMIL | Loan |
| 31 Jan 13 | P. Bamford Patrick Bamford | ChelseaCHE | → | Milton Keynes DonsMKD | Loan |
| 15 Jan 13 | L. Piazon Lucas Piazon | ChelseaCHE | → |  MálagaMCF | Loan |
| 15 Jan 13 | L. Piazon Lucas Piazon | ChelseaCHE | → | MálagaMCF | Loan |
| 14 Jan 13 | S. Walker Sam Walker | ChelseaCHE | → | Colchester UnitedCOL | Loan |
| 11 Jan 13 | B. Clifford Billy Clifford | ChelseaCHE | → | Colchester UnitedCOL | Loan |
| 09 Jan 13 | T. Kane Todd Kane | ChelseaCHE | → | Blackburn RoversBLK | Loan |
| 09 Jan 13 | T. Kane Todd Kane | ChelseaCHE | → | Blackburn RoversBLK | Loan |
| 04 Jan 13 | D. Ba Demba Ba |  Newcastle UnitedNEW | → | ChelseaCHE | Undisclosed |
| 02 Jan 13 | D. Sturridge Daniel Sturridge | ChelseaCHE | → | LiverpoolLIV | Undisclosed |
| 01 Jan 13 | W. Oliveira Wallace Oliveira |  FluminenseFLU | → | ChelseaCHE | Undisclosed |
| 01 Jan 13 | W. Oliveira Wallace Oliveira | ChelseaCHE | → | FluminenseFLU | Loan |
| 01 Jan 13 | W. Oliveira Wallace Oliveira | FluminenseFLU | → | ChelseaCHE | Undisclosed |
| 01 Jan 13 | W. Oliveira Wallace Oliveira | ChelseaCHE | → | FluminenseFLU | Loan |