| 16 Oct 20 | J. Clark-Salter Jake Clark-Salter |  ChelseaCHE | → |  Birmingham CityBIR | Loan |
| 16 Oct 20 | J. Clark-Salter Jake Clark-Salter | ChelseaCHE | → | Birmingham CityBIR | Loan |
| 15 Oct 20 | V. Moses Victor Moses | ChelseaCHE | → |  Spartak MoscowSPM | Loan |
| 13 Oct 20 | I. Maatsen Ian Maatsen | ChelseaCHE | → |  Charlton AthleticCHA | Loan |
| 09 Oct 20 | N. Baxter Nathan Baxter | ChelseaCHE | → |  Accrington StanleyACCR | Loan |
| 06 Oct 20 | M. Sarr Malang Sarr | ChelseaCHE | → |  FC PortoPOR | Loan |
| 06 Oct 20 | J. Familia-Castillo Juan Familia-Castillo | ChelseaCHE | → |  AZ AlkmaarAZ | Loan |
| 06 Oct 20 | M. van Ginkel Marco van Ginkel | ChelseaCHE | → |  PSV EindhovenPSV | Loan |
| 06 Oct 20 | J. Familia-Castillo Juan Familia-Castillo | ChelseaCHE | → | AZ AlkmaarAZ | Loan |
| 06 Oct 20 | M. van Ginkel Marco van Ginkel | ChelseaCHE | → | PSV EindhovenPSV | Loan |
| 05 Oct 20 | R. Loftus-Cheek Ruben Loftus-Cheek | ChelseaCHE | → |  FulhamFUL | Loan |
| 05 Oct 20 | T. Bakayoko Tiemoué Bakayoko | ChelseaCHE | → |  NapoliNAP | Loan |
| 05 Oct 20 | T. Bakayoko Tiemoué Bakayoko | ChelseaCHE | → | NapoliNAP | Loan |
| 03 Oct 20 | M. Miazga Matt Miazga | ChelseaCHE | → |  AnderlechtAND | Loan |
| 02 Oct 20 | J. Russell Jonathan Russell | ChelseaCHE | → | Accrington StanleyACCR | Loan |
| 30 Sept 20 | R. Barkley Ross Barkley | ChelseaCHE | → |  Aston VillaAVL | Loan |
| 24 Sept 20 | É. Mendy Édouard Mendy |  Stade RennaisREN | → | ChelseaCHE | Undisclosed |
| 24 Sept 20 | É. Mendy Édouard Mendy | Stade RennaisREN | → | ChelseaCHE | Undisclosed |
| 21 Sept 20 | L. Mccormick Luke Mccormick | ChelseaCHE | → |  Bristol RoversBRI | Loan |
| 19 Sept 20 | D. Zappacosta Davide Zappacosta | ChelseaCHE | → |  GenoaGEN | Loan |
| 19 Sept 20 | D. Zappacosta Davide Zappacosta | ChelseaCHE | → | GenoaGEN | Loan |
| 18 Sept 20 | L. Baker Lewis Baker | ChelseaCHE | → |  TrabzonsporTRAB | Loan |
| 17 Sept 20 | C. Gallagher Conor Gallagher | ChelseaCHE | → |  West Bromwich AlbionWBA | Loan |
| 10 Sept 20 | M. Batshuayi Michy Batshuayi | ChelseaCHE | → |  Crystal PalaceCRY | Loan |
| 08 Sept 20 | Kenedy | ChelseaCHE | → |  GranadaGCF | Loan |
| 08 Sept 20 | Kenedy | ChelseaCHE | → | GranadaGCF | Loan |
| 07 Sept 20 | T. Uwakwe Tariq Uwakwe | ChelseaCHE | → | Accrington StanleyACCR | Loan |
| 07 Sept 20 | E. Ampadu Ethan Ampadu | ChelseaCHE | → |  Sheffield UnitedSHU | Loan |
| 04 Sept 20 | K. Havertz Kai Havertz |  Bayer LeverkusenLEV | → | ChelseaCHE | Undisclosed |
| 04 Sept 20 | K. Havertz Kai Havertz | Bayer LeverkusenLEV | → | ChelseaCHE | Undisclosed |
| 28 Aug 20 | T. Silva Thiago Silva |  Paris Saint-Germain PSG | → | ChelseaCHE | Free |
| 28 Aug 20 | T. Silva Thiago Silva | Paris Saint-Germain PSG | → | ChelseaCHE | Free |
| 27 Aug 20 | M. Sarr Malang Sarr | XXX | → | ChelseaCHE | Free |
| 26 Aug 20 | M. Guehi Marc Guehi | ChelseaCHE | → |  Swansea CitySWA | Loan |
| 26 Aug 20 | M. Guehi Marc Guehi | ChelseaCHE | → | Swansea CitySWA | Loan |
| 26 Aug 20 | B. Chilwell Ben Chilwell |  Leicester CityLEI | → | ChelseaCHE | Undisclosed |
| 25 Aug 20 | Pedro | ChelseaCHE | → |  AS RomaROMA | Free |
| 25 Aug 20 | Pedro | ChelseaCHE | → | AS RomaROMA | Free |
| 24 Aug 20 | J. Blackman Jamal Blackman | ChelseaCHE | → |  Rotherham UnitedROT | Loan |
| 24 Aug 20 | J. Blackman Jamal Blackman | ChelseaCHE | → | Rotherham UnitedROT | Loan |
| 21 Aug 20 | A. Broja Armando Broja | ChelseaCHE | → |  VitesseVIT | Loan |
| 21 Aug 20 | A. Broja Armando Broja | ChelseaCHE | → | VitesseVIT | Loan |
| 20 Aug 20 | I. Brown Isaiah Brown | ChelseaCHE | → |  Sheffield WednesdaySHW | Loan |
| 20 Aug 20 | I. Brown Isaiah Brown | ChelseaCHE | → | Sheffield WednesdaySHW | Loan |
| 20 Aug 20 | X. Mbuyamba Xavier Mbuyamba | XXX | → | ChelseaCHE | Free |
| 18 Aug 20 | T. Chalobah Trevoh Chalobah | ChelseaCHE | → |  LorientLOR | Loan |
| 18 Aug 20 | T. Chalobah Trevoh Chalobah | ChelseaCHE | → | LorientLOR | Loan |
| 18 Aug 20 | I. Ugbo Ike Ugbo | ChelseaCHE | → |  Cercle Brugge KSVCBK | Loan |
| 17 Aug 20 | J. Cumming Jamie Cumming | ChelseaCHE | → |  StevenageSTE | Loan |
| 14 Aug 20 | Willian | ChelseaCHE | → |  ArsenalARS | Free |
| 01 Jul 20 | Nathan | ChelseaCHE | → |  Atlético-MGCAM | Undisclosed |
| 01 Jul 20 | H. Ziyech Hakim Ziyech |  Ajax AmsterdamAJA | → | ChelseaCHE | 44000000 |
| 01 Jul 20 | Nathan | ChelseaCHE | → | Atlético-MGCAM | Undisclosed |
| 01 Jul 20 | Á. Morata Álvaro Morata | ChelseaCHE | → |  Atletico MadridATL | Undisclosed |
| 01 Jul 20 | M. Pasalic Mario Pasalic | ChelseaCHE | → |  AtalantaATA | Undisclosed |
| 01 Jul 20 | T. Werner Timo Werner |  RB LeipzigRBL | → | ChelseaCHE | Undisclosed |
| 01 Jul 20 | Á. Morata Álvaro Morata | ChelseaCHE | → | Atletico MadridATL | Undisclosed |
| 01 Jul 20 | M. Pasalic Mario Pasalic | ChelseaCHE | → | AtalantaATA | Undisclosed |
| 01 Jul 20 | T. Werner Timo Werner | RB LeipzigRBL | → | ChelseaCHE | Undisclosed |
| 01 Jul 20 | H. Ziyech Hakim Ziyech | Ajax AmsterdamAJA | → | ChelseaCHE | 44000000 |
| 31 Jan 20 | T. Lamptey Tariq Lamptey | ChelseaCHE | → |  Brighton & Hove AlbionBHA | Undisclosed |
| 31 Jan 20 | C. Brown Charlie Brown | ChelseaCHE | → | RUSRoyale Union Saint-GilloiseRoyale Union Saint-Gilloise | Loan |
| 31 Jan 20 | C. Mola Clinton Mola | ChelseaCHE | → |  VfB StuttgartVFB | Undisclosed |
| 30 Jan 20 | G. McEachran George McEachran | ChelseaCHE | → |  SC CambuurCAM | Loan |
| 23 Jan 20 | V. Moses Victor Moses | ChelseaCHE | → |  InternazionaleINT | Loan |
| 23 Jan 20 | V. Moses Victor Moses | ChelseaCHE | → | InternazionaleINT | Loan |
| 22 Jan 20 | J. Blackman Jamal Blackman | ChelseaCHE | → | Bristol RoversBRI | Loan |
| 15 Jan 20 | C. Gallagher Conor Gallagher | ChelseaCHE | → | Swansea CitySWA | Loan |
| 15 Jan 20 | C. Gallagher Conor Gallagher | ChelseaCHE | → | Swansea CitySWA | Loan |
| 10 Jan 20 | M. Guehi Marc Guehi | ChelseaCHE | → | Swansea CitySWA | Loan |
| 10 Jan 20 | M. Guehi Marc Guehi | ChelseaCHE | → | Swansea CitySWA | Loan |
| 07 Jan 20 | D. Drinkwater Danny Drinkwater | ChelseaCHE | → | Aston VillaAVL | Loan |
| 01 Jan 20 | M. Hector Michael Hector | ChelseaCHE | → | FulhamFUL | Undisclosed |
| 01 Jan 20 | M. Hector Michael Hector | ChelseaCHE | → | FulhamFUL | Undisclosed |