| 20 Nov 09 | R. Taylor Rhys Taylor |  ChelseaCHE | → |  Queens Park RangersQPR | Loan |
| 20 Nov 09 | R. Taylor Rhys Taylor | ChelseaCHE | → | Queens Park RangersQPR | Loan |
| 13 Nov 09 | S. Ofori-Twumasi Seth Ofori-Twumasi | ChelseaCHE | → |  Dagenham & RedbridgeD&R | Loan |
| 01 Sept 09 | S. Cummings Shaun Cummings | ChelseaCHE | → |  ReadingREA | Undisclosed |
| 01 Sept 09 | S. Cummings Shaun Cummings | ChelseaCHE | → | ReadingREA | Undisclosed |
| 21 Aug 09 | J. Cork Jack Cork | ChelseaCHE | → |  Coventry CityCOV | Loan |
| 21 Aug 09 | J. Cork Jack Cork | ChelseaCHE | → | Coventry CityCOV | Loan |
| 18 Aug 09 | C. Pizarro Claudio Pizarro | ChelseaCHE | → |  Werder BremenWER | Undisclosed |
| 18 Aug 09 | C. Pizarro Claudio Pizarro | ChelseaCHE | → | Werder BremenWER | Undisclosed |
| 18 Aug 09 | N. Matic Nemanja Matic | MKXMFK KosiceMFK Kosice | → | ChelseaCHE | Undisclosed |
| 17 Aug 09 | S. Cummings Shaun Cummings | ChelseaCHE | → |  West Bromwich AlbionWBA | Loan |
| 17 Aug 09 | S. Cummings Shaun Cummings | ChelseaCHE | → | West Bromwich AlbionWBA | Loan |
| 14 Aug 09 | J. Mellis Jacob Mellis | ChelseaCHE | → |  SouthamptonSOU | Loan |
| 13 Aug 09 | M. Mancienne Michael Mancienne | ChelseaCHE | → |  Wolverhampton WanderersWOL | Loan |
| 07 Aug 09 | P. van Aanholt Patrick van Aanholt | ChelseaCHE | → | Coventry CityCOV | Loan |
| 07 Aug 09 | P. van Aanholt Patrick van Aanholt | ChelseaCHE | → | Coventry CityCOV | Loan |
| 06 Aug 09 | S. Sinclair Scott Sinclair | ChelseaCHE | → |  Wigan AthleticWGA | Loan |
| 03 Aug 09 | F. Di Santo Franco Di Santo | ChelseaCHE | → |  Blackburn RoversBLK | Loan |
| 24 Jul 09 | Sergio Tejera | ChelseaCHE | → |  MallorcaMLL | Undisclosed |
| 24 Jul 09 | Sergio Tejera | ChelseaCHE | → | MallorcaMLL | Undisclosed |
| 22 Jul 09 | F. Nouble Frank Nouble | ChelseaCHE | → |  West Ham UnitedWHU | Undisclosed |
| 18 Jul 09 | R. Bertrand Ryan Bertrand | ChelseaCHE | → | ReadingREA | Loan |
| 18 Jul 09 | R. Bertrand Ryan Bertrand | ChelseaCHE | → | ReadingREA | Loan |
| 16 Jul 09 | M. Stoch Miroslav Stoch | ChelseaCHE | → |  FC TwenteTWE | Loan |
| 16 Jul 09 | M. Stoch Miroslav Stoch | ChelseaCHE | → | FC TwenteTWE | Loan |
| 14 Jul 09 | L. Sawyer Lee Sawyer | ChelseaCHE | → |  Southend UnitedSOUT | Loan |
| 09 Jul 09 | J. Smith Jimmy Smith | ChelseaCHE | → |  Leyton OrientLEY | Free |
| 09 Jul 09 | T. Taiwo Tom Taiwo | ChelseaCHE | → |  Carlisle UnitedCAR | Loan |
| 07 Jul 09 | Y. Zhirkov Yuri Zhirkov |  CSKA MoscowCSK | → | ChelseaCHE | 18000000 |
| 02 Jul 09 | R. Turnbull Ross Turnbull |  MiddlesbroughMID | → | ChelseaCHE | Free |
| 02 Jul 09 | R. Turnbull Ross Turnbull | MiddlesbroughMID | → | ChelseaCHE | Free |
| 22 Jun 09 | B. Sahar Ben Sahar | ChelseaCHE | → |  EspanyolESP | Undisclosed |
| 22 Jun 09 | B. Sahar Ben Sahar | ChelseaCHE | → | EspanyolESP | Undisclosed |
| 19 Mar 09 | L. Sawyer Lee Sawyer | ChelseaCHE | → |  Wycombe WanderersWYC | Loan |
| 20 Feb 09 | Fabio Ferreira | ChelseaCHE | → |  Oldham AthleticOLD | Loan |
| 02 Feb 09 | R. Quaresma Ricardo Quaresma |  InternazionaleINT | → | ChelseaCHE | Loan |
| 02 Feb 09 | Sergio Tejera | ChelseaCHE | → | MallorcaMLL | Loan |
| 02 Feb 09 | J. Smith Jimmy Smith | ChelseaCHE | → | Leyton OrientLEY | Loan |
| 02 Feb 09 | Sergio Tejera | ChelseaCHE | → | MallorcaMLL | Loan |
| 02 Feb 09 | R. Quaresma Ricardo Quaresma | InternazionaleINT | → | ChelseaCHE | Loan |
| 30 Jan 09 | G. Töre Gökhan Töre |  Bayer LeverkusenLEV | → | ChelseaCHE | Undisclosed |
| 30 Jan 09 | G. Töre Gökhan Töre | Bayer LeverkusenLEV | → | ChelseaCHE | Undisclosed |
| 30 Jan 09 | C. Magney Carl Magney | ChelseaCHE | → |  Milton Keynes DonsMKD | Loan |
| 26 Jan 09 | L. Sawyer Lee Sawyer | ChelseaCHE | → | Coventry CityCOV | Loan |
| 26 Jan 09 | L. Sawyer Lee Sawyer | ChelseaCHE | → | Coventry CityCOV | Loan |
| 26 Jan 09 | C. Cudicini Carlo Cudicini | ChelseaCHE | → |  Tottenham HotspurTOT | Free |
| 06 Jan 09 | S. Sinclair Scott Sinclair | ChelseaCHE | → |  Birmingham CityBIR | Loan |
| 06 Jan 09 | S. Sinclair Scott Sinclair | ChelseaCHE | → | Birmingham CityBIR | Loan |
| 03 Jan 09 | B. Sahar Ben Sahar | ChelseaCHE | → |  De GraafschapGRA | Loan |
| 03 Jan 09 | W. Bridge Wayne Bridge | ChelseaCHE | → |  Manchester CityMNC | Undisclosed |
| 03 Jan 09 | B. Sahar Ben Sahar | ChelseaCHE | → | De GraafschapGRA | Loan |
| 02 Jan 09 | J. Cork Jack Cork | ChelseaCHE | → |  WatfordWAT | Loan |
| 02 Jan 09 | J. Cork Jack Cork | ChelseaCHE | → | WatfordWAT | Loan |