| 25 Nov 10 | M. Woods Michael Woods |  ChelseaCHE | → |  Notts CountyNOTT | Loan |
| 15 Nov 10 | Adam Phillip | ChelseaCHE | → |  Yeovil TownYEO | Loan |
| 22 Oct 10 | C. Clifford Conor Clifford | ChelseaCHE | → |  Plymouth ArgylePLY | Loan |
| 31 Aug 10 | Matej Delac | ZXXZapresic Zapresic | → | ChelseaCHE | Undisclosed |
| 31 Aug 10 | F. Di Santo Franco Di Santo | ChelseaCHE | → |  Wigan AthleticWGA | Undisclosed |
| 31 Aug 10 | Matej Delac | ChelseaCHE | → |  VitesseVIT | Loan |
| 31 Aug 10 | Matej Delac | ChelseaCHE | → | VitesseVIT | Loan |
| 26 Aug 10 | M. Mancienne Michael Mancienne | ChelseaCHE | → |  Wolverhampton WanderersWOL | Loan |
| 24 Aug 10 | N. Matic Nemanja Matic | ChelseaCHE | → | VitesseVIT | Loan |
| 24 Aug 10 | S. Rajkovic Slobodan Rajkovic | ChelseaCHE | → | VitesseVIT | Loan |
| 24 Aug 10 | S. Rajkovic Slobodan Rajkovic | ChelseaCHE | → | VitesseVIT | Loan |
| 24 Aug 10 | N. Matic Nemanja Matic | ChelseaCHE | → | VitesseVIT | Loan |
| 13 Aug 10 | Ramires |  BenficaBEN | → | ChelseaCHE | Undisclosed |
| 12 Aug 10 | R. Carvalho Ricardo Carvalho | ChelseaCHE | → |  Real MadridMAD | Undisclosed |
| 12 Aug 10 | R. Carvalho Ricardo Carvalho | ChelseaCHE | → | Real MadridMAD | Undisclosed |
| 12 Aug 10 | J. Cork Jack Cork | ChelseaCHE | → |  BurnleyBUR | Loan |
| 12 Aug 10 | J. Cork Jack Cork | ChelseaCHE | → | BurnleyBUR | Loan |
| 09 Aug 10 | S. Sinclair Scott Sinclair | ChelseaCHE | → |  Swansea CitySWA | 500000 |
| 09 Aug 10 | S. Sinclair Scott Sinclair | ChelseaCHE | → | Swansea CitySWA | 500000 |
| 07 Aug 10 | A. Deco Deco | ChelseaCHE | → |  FluminenseFLU | Undisclosed |
| 07 Aug 10 | A. Deco Deco | ChelseaCHE | → | FluminenseFLU | Undisclosed |
| 05 Aug 10 | R. Bertrand Ryan Bertrand | ChelseaCHE | → |  Nottingham ForestFOR | Loan |
| 05 Aug 10 | R. Bertrand Ryan Bertrand | ChelseaCHE | → | Nottingham ForestFOR | Loan |
| 05 Aug 10 | B. Gordon Ben Gordon | ChelseaCHE | → |  KilmarnockKIL | Loan |
| 05 Aug 10 | B. Gordon Ben Gordon | ChelseaCHE | → | KilmarnockKIL | Loan |
| 02 Aug 10 | D. Philliskirk Danny Philliskirk | ChelseaCHE | → |  Oxford UnitedOXF | Loan |
| 06 Jul 10 | R. Taylor Rhys Taylor | ChelseaCHE | → |  Crewe AlexandraCREW | Loan |
| 02 Jul 10 | Y. Benayoun Yossi Benayoun |  LiverpoolLIV | → | ChelseaCHE | Undisclosed |
| 01 Jul 10 | S. Ofori-Twumasi Seth Ofori-Twumasi | ChelseaCHE | → |  Peterborough UnitedPET | Free |
| 01 Jul 10 | M. Ballack Michael Ballack | ChelseaCHE | → |  Bayer LeverkusenLEV | Free |
| 01 Jul 10 | M. Ballack Michael Ballack | ChelseaCHE | → | Bayer LeverkusenLEV | Free |
| 25 Mar 10 | B. Gordon Ben Gordon | ChelseaCHE | → |  Tranmere RoversTRN | Loan |
| 01 Feb 10 | J. Cork Jack Cork | ChelseaCHE | → | BurnleyBUR | Loan |
| 29 Jan 10 | P. van Aanholt Patrick van Aanholt | ChelseaCHE | → |  Newcastle UnitedNEW | Loan |
| 29 Jan 10 | P. van Aanholt Patrick van Aanholt | ChelseaCHE | → | Newcastle UnitedNEW | Loan |
| 06 Jan 10 | T. Taiwo Tom Taiwo | ChelseaCHE | → |  Carlisle UnitedCAR | Undisclosed |