| 02 Sept 19 | B. Rahman Baba Rahman |  ChelseaCHE | → |  MallorcaMLL | Loan |
| 02 Sept 19 | B. Rahman Baba Rahman | ChelseaCHE | → | MallorcaMLL | Loan |
| 02 Sept 19 | Kenedy | ChelseaCHE | → |  GetafeGET | Loan |
| 02 Sept 19 | Kenedy | ChelseaCHE | → | GetafeGET | Loan |
| 31 Aug 19 | T. Bakayoko Tiemoué Bakayoko | ChelseaCHE | → |  AS MonacoMON | Loan |
| 31 Aug 19 | T. Bakayoko Tiemoué Bakayoko | ChelseaCHE | → | AS MonacoMON | Loan |
| 30 Aug 19 | Juan Castillo | ChelseaCHE | → |  Ajax AmsterdamAJA | Loan |
| 30 Aug 19 | Juan Castillo | ChelseaCHE | → | Ajax AmsterdamAJA | Loan |
| 21 Aug 19 | D. Zappacosta Davide Zappacosta | ChelseaCHE | → |  AS RomaROMA | Loan |
| 21 Aug 19 | D. Zappacosta Davide Zappacosta | ChelseaCHE | → | AS RomaROMA | Loan |
| 08 Aug 19 | D. Luiz David Luiz | ChelseaCHE | → |  ArsenalARS | Undisclosed |
| 08 Aug 19 | T. Chalobah Trevoh Chalobah | ChelseaCHE | → |  Huddersfield TownHUD | Loan |
| 08 Aug 19 | I. Brown Isaiah Brown | ChelseaCHE | → |  Luton TownLUT | Loan |
| 08 Aug 19 | T. Chalobah Trevoh Chalobah | ChelseaCHE | → | Huddersfield TownHUD | Loan |
| 08 Aug 19 | I. Brown Isaiah Brown | ChelseaCHE | → | Luton TownLUT | Loan |
| 08 Aug 19 | J. Maddox Jacob Maddox | ChelseaCHE | → |  Tranmere RoversTRN | Loan |
| 08 Aug 19 | J. Grant Josh Grant | ChelseaCHE | → |  Plymouth ArgylePLY | Loan |
| 08 Aug 19 | D. Drinkwater Danny Drinkwater | ChelseaCHE | → |  BurnleyBUR | Loan |
| 02 Aug 19 | C. Gallagher Conor Gallagher | ChelseaCHE | → |  Charlton AthleticCHA | Loan |
| 02 Aug 19 | C. Gallagher Conor Gallagher | ChelseaCHE | → | Charlton AthleticCHA | Loan |
| 01 Aug 19 | K. Palmer Kasey Palmer | ChelseaCHE | → |  Bristol CityBRC | Undisclosed |
| 01 Aug 19 | D. Sterling Dujon Sterling | ChelseaCHE | → |  Wigan AthleticWGA | Loan |
| 01 Aug 19 | K. Palmer Kasey Palmer | ChelseaCHE | → | Bristol CityBRC | Undisclosed |
| 01 Aug 19 | D. Sterling Dujon Sterling | ChelseaCHE | → | Wigan AthleticWGA | Loan |
| 29 Jul 19 | K. Scott Kyle Scott | ChelseaCHE | → |  Newcastle UnitedNEW | Free |
| 27 Jul 19 | T. Kane Todd Kane | ChelseaCHE | → |  Queens Park RangersQPR | Free |
| 27 Jul 19 | T. Kane Todd Kane | ChelseaCHE | → | Queens Park RangersQPR | Free |
| 24 Jul 19 | M. Miazga Matt Miazga | ChelseaCHE | → |  ReadingREA | Loan |
| 24 Jul 19 | L. Baker Lewis Baker | ChelseaCHE | → |  Fortuna DüsseldorfFOR | Loan |
| 24 Jul 19 | M. Miazga Matt Miazga | ChelseaCHE | → | ReadingREA | Loan |
| 24 Jul 19 | J. Clark-Salter Jake Clark-Salter | ChelseaCHE | → |  Birmingham CityBIR | Loan |
| 24 Jul 19 | L. Baker Lewis Baker | ChelseaCHE | → | Fortuna DüsseldorfFOR | Loan |
| 24 Jul 19 | J. Clark-Salter Jake Clark-Salter | ChelseaCHE | → | Birmingham CityBIR | Loan |
| 22 Jul 19 | E. Ampadu Ethan Ampadu | ChelseaCHE | → |  RB LeipzigRBL | Loan |
| 22 Jul 19 | E. Ampadu Ethan Ampadu | ChelseaCHE | → | RB LeipzigRBL | Loan |
| 18 Jul 19 | L. McCormick Luke McCormick | ChelseaCHE | → |  Shrewsbury TownSHR | Loan |
| 06 Jul 19 | M. Bulka Marcin Bulka | ChelseaCHE | → |  Paris Saint-Germain PSG | Free |
| 06 Jul 19 | M. Bulka Marcin Bulka | ChelseaCHE | → | Paris Saint-Germain PSG | Free |
| 01 Jul 19 | O. Aina Ola Aina | ChelseaCHE | → |  TorinoTOR | Undisclosed |
| 01 Jul 19 | T. Kalas Tomás Kalas | ChelseaCHE | → | Bristol CityBRC | Undisclosed |
| 01 Jul 19 | E. Hazard Eden Hazard | ChelseaCHE | → |  Real MadridMAD | Undisclosed |
| 01 Jul 19 | T. Kalas Tomás Kalas | ChelseaCHE | → | Bristol CityBRC | Undisclosed |
| 01 Jul 19 | M. Kovacic Mateo Kovacic | Real MadridMAD | → | ChelseaCHE | Undisclosed |
| 01 Jul 19 | R. Nartey Richard Nartey | ChelseaCHE | → |  Burton AlbionBRT | Loan |
| 01 Jul 19 | B. Collins Bradley Collins | ChelseaCHE | → |  BarnsleyBAR | Free |
| 01 Jul 19 | O. Aina Ola Aina | ChelseaCHE | → | TorinoTOR | Undisclosed |
| 01 Jul 19 | E. Hazard Eden Hazard | ChelseaCHE | → | Real MadridMAD | Undisclosed |
| 01 Jul 19 | M. Kovacic Mateo Kovacic | Real MadridMAD | → | ChelseaCHE | Undisclosed |
| 26 Jun 19 | J. Da Silva Jay Da Silva | ChelseaCHE | → | Bristol CityBRC | Undisclosed |
| 26 Jun 19 | J. Da Silva Jay Da Silva | ChelseaCHE | → | Bristol CityBRC | Undisclosed |
| 31 Jan 19 | L. Piazon Lucas Piazon | ChelseaCHE | → |  Chievo VeronaCVO | Loan |
| 31 Jan 19 | L. Piazon Lucas Piazon | ChelseaCHE | → | Chievo VeronaCVO | Loan |
| 31 Jan 19 | M. Batshuayi Michy Batshuayi | ChelseaCHE | → |  Crystal PalaceCRY | Loan |
| 28 Jan 19 | Á. Morata Álvaro Morata | ChelseaCHE | → |  Atletico MadridATL | Loan |
| 28 Jan 19 | Á. Morata Álvaro Morata | ChelseaCHE | → | Atletico MadridATL | Loan |
| 25 Jan 19 | V. Moses Victor Moses | ChelseaCHE | → |  FenerbahceFEN | Loan |
| 25 Jan 19 | M. Miazga Matt Miazga | ChelseaCHE | → | ReadingREA | Loan |
| 25 Jan 19 | M. Miazga Matt Miazga | ChelseaCHE | → | ReadingREA | Loan |
| 23 Jan 19 | G. Higuaín Gonzalo Higuaín |  JuventusJUV | → | ChelseaCHE | Loan |
| 23 Jan 19 | G. Higuaín Gonzalo Higuaín | JuventusJUV | → | ChelseaCHE | Loan |
| 11 Jan 19 | C. Fàbregas Cesc Fàbregas | ChelseaCHE | → | AS MonacoMON | Undisclosed |
| 11 Jan 19 | C. Fàbregas Cesc Fàbregas | ChelseaCHE | → | AS MonacoMON | Undisclosed |
| 11 Jan 19 | J. Grant Josh Grant | ChelseaCHE | → |  Yeovil TownYEO | Loan |
| 09 Jan 19 | L. Baker Lewis Baker | ChelseaCHE | → | ReadingREA | Loan |
| 09 Jan 19 | K. Palmer Kasey Palmer | ChelseaCHE | → | Bristol CityBRC | Loan |
| 09 Jan 19 | K. Palmer Kasey Palmer | ChelseaCHE | → | Bristol CityBRC | Loan |
| 09 Jan 19 | L. Baker Lewis Baker | ChelseaCHE | → | ReadingREA | Loan |
| 02 Jan 19 | C. Pulisic Christian Pulisic |  Borussia DortmundDOR | → | ChelseaCHE | 64000000 |
| 02 Jan 19 | C. Pulisic Christian Pulisic | Borussia DortmundDOR | → | ChelseaCHE | 64000000 |
| 02 Jan 19 | C. Pulisic Christian Pulisic | ChelseaCHE | → | Borussia DortmundDOR | Loan |
| 02 Jan 19 | C. Pulisic Christian Pulisic | ChelseaCHE | → | Borussia DortmundDOR | Loan |