| 27 Nov 08 | L. Bridcutt Liam Bridcutt |  ChelseaCHE | → |  WatfordWAT | Loan |
| 27 Nov 08 | L. Bridcutt Liam Bridcutt | ChelseaCHE | → | WatfordWAT | Loan |
| 27 Oct 08 | M. Mancienne Michael Mancienne | ChelseaCHE | → |  Wolverhampton WanderersWOL | Loan |
| 27 Oct 08 | M. Mancienne Michael Mancienne | ChelseaCHE | → | Wolverhampton WanderersWOL | Loan |
| 24 Sept 08 | C. da Silva Mineiro | XXX | → | ChelseaCHE | Free |
| 29 Aug 08 | T. Taiwo Tom Taiwo | ChelseaCHE | → |  Port ValeVALE | Loan |
| 28 Aug 08 | S. Wright-Phillips Shaun Wright-Phillips | ChelseaCHE | → |  Manchester CityMNC | Undisclosed |
| 25 Aug 08 | A. Shevchenko Andriy Shevchenko | ChelseaCHE | → |  AC MilanMIL | Undisclosed |
| 25 Aug 08 | A. Shevchenko Andriy Shevchenko | ChelseaCHE | → | AC MilanMIL | Undisclosed |
| 21 Aug 08 | J. Cork Jack Cork | ChelseaCHE | → |  SouthamptonSOU | Loan |
| 21 Aug 08 | J. Cork Jack Cork | ChelseaCHE | → | SouthamptonSOU | Loan |
| 21 Aug 08 | F. Paim Fábio Paim |  Sporting CPSCP | → | ChelseaCHE | Loan |
| 18 Aug 08 | L. Sawyer Lee Sawyer | ChelseaCHE | → |  Southend UnitedSOUT | Loan |
| 15 Aug 08 | C. Pizarro Claudio Pizarro | ChelseaCHE | → |  Werder BremenWER | Loan |
| 15 Aug 08 | C. Pizarro Claudio Pizarro | ChelseaCHE | → | Werder BremenWER | Loan |
| 08 Aug 08 | Eduardo Alcides | ChelseaCHE | → | DDXDnipro Dnipropetrovsk Dnipro Dnipropetrovsk | Loan |
| 07 Aug 08 | A. Grant Anthony Grant | ChelseaCHE | → | Southend UnitedSOUT | Free |
| 04 Aug 08 | S. Cummings Shaun Cummings | ChelseaCHE | → |  Milton Keynes DonsMKD | Loan |
| 30 Jul 08 | T. Ben Haim Tal Ben Haim | ChelseaCHE | → | Manchester CityMNC | Undisclosed |
| 21 Jul 08 | K. Boulahrouz Khalid Boulahrouz | ChelseaCHE | → |  VfB StuttgartVFB | Undisclosed |
| 21 Jul 08 | C. Makelele Claude Makelele | ChelseaCHE | → |  Paris Saint-Germain PSG | Free |
| 21 Jul 08 | K. Boulahrouz Khalid Boulahrouz | ChelseaCHE | → | VfB StuttgartVFB | Undisclosed |
| 21 Jul 08 | C. Makelele Claude Makelele | ChelseaCHE | → | Paris Saint-Germain PSG | Free |
| 10 Jul 08 | S. Sidwell Steve Sidwell | ChelseaCHE | → |  Aston VillaAVL | 5500000 |
| 09 Jul 08 | S. Rajkovic Slobodan Rajkovic | ChelseaCHE | → |  FC TwenteTWE | Loan |
| 09 Jul 08 | S. Rajkovic Slobodan Rajkovic | ChelseaCHE | → | FC TwenteTWE | Loan |
| 05 Jul 08 | R. Bertrand Ryan Bertrand | ChelseaCHE | → |  Norwich CityNOR | Free |
| 05 Jul 08 | R. Bertrand Ryan Bertrand | ChelseaCHE | → | Norwich CityNOR | Free |
| 01 Jul 08 | J. Smith Jimmy Smith | ChelseaCHE | → |  Sheffield WednesdaySHW | Loan |
| 01 Jul 08 | B. Sahar Ben Sahar | ChelseaCHE | → |  PortsmouthPOR | Loan |
| 01 Jul 08 | J. Smith Jimmy Smith | ChelseaCHE | → | Sheffield WednesdaySHW | Loan |
| 30 Jun 08 | A. Deco Deco |  BarcelonaBAR | → | ChelseaCHE | Undisclosed |
| 30 Jun 08 | A. Deco Deco | BarcelonaBAR | → | ChelseaCHE | Undisclosed |
| 12 May 08 | J. Bosingwa José Bosingwa |  FC PortoPOR | → | ChelseaCHE | 16200000 |
| 08 May 08 | H. Worley Harry Worley | ChelseaCHE | → |  Leicester CityLEI | Free |
| 27 Mar 08 | S. Sinclair Scott Sinclair | ChelseaCHE | → |  Crystal PalaceCRY | Loan |
| 27 Mar 08 | S. Sinclair Scott Sinclair | ChelseaCHE | → | Crystal PalaceCRY | Loan |
| 07 Mar 08 | J. Simmonds James Simmonds | ChelseaCHE | → | DAXDover AthleticDover Athletic | Loan |
| 07 Mar 08 | H. Worley Harry Worley | ChelseaCHE | → | Leicester CityLEI | Loan |
| 28 Feb 08 | S. Sinclair Scott Sinclair | ChelseaCHE | → |  Charlton AthleticCHA | Loan |
| 28 Feb 08 | S. Sinclair Scott Sinclair | ChelseaCHE | → | Charlton AthleticCHA | Loan |
| 21 Feb 08 | B. Sahar Ben Sahar | ChelseaCHE | → |  Queens Park RangersQPR | Loan |
| 21 Feb 08 | B. Sahar Ben Sahar | ChelseaCHE | → | Queens Park RangersQPR | Loan |
| 08 Feb 08 | L. Bridcutt Liam Bridcutt | ChelseaCHE | → |  Yeovil TownYEO | Loan |
| 31 Jan 08 | A. Grant Anthony Grant | ChelseaCHE | → | Southend UnitedSOUT | Loan |
| 30 Jan 08 | A. Pettigrew Adrian Pettigrew | ChelseaCHE | → |  Rotherham UnitedROT | Loan |
| 25 Jan 08 | F. Di Santo Franco Di Santo |  Audax ItalianoAUD | → | ChelseaCHE | Undisclosed |
| 16 Jan 08 | B. Ivanovic Branislav Ivanovic |  Lokomotiv MoscowLMO | → | ChelseaCHE | Undisclosed |
| 11 Jan 08 | N. Anelka Nicolas Anelka |  Bolton WanderersBOL | → | ChelseaCHE | 15000000 |
| 04 Jan 08 | R. Bertrand Ryan Bertrand | ChelseaCHE | → | Norwich CityNOR | Loan |
| 04 Jan 08 | R. Bertrand Ryan Bertrand | ChelseaCHE | → | Norwich CityNOR | Loan |