| Date | Player | From | To | Amount |
|---|---|---|---|---|
| 02 Sept 19 | Cameron Borthwick-Jackson | Loan | ||
| 02 Sept 19 | Lee O'Connor | Undisclosed | ||
| 02 Sept 19 | Matteo Darmian | Undisclosed | ||
| 02 Sept 19 | Matteo Darmian | Undisclosed | ||
| 02 Sept 19 | Lee O'Connor | Undisclosed | ||
| 30 Aug 19 | Chris Smalling | Loan | ||
| 30 Aug 19 | Chris Smalling | Loan | ||
| 29 Aug 19 | Alexis Sánchez | Loan | ||
| 29 Aug 19 | Alexis Sánchez | Loan | ||
| 16 Aug 19 | Ethan Hamilton | Loan | ||
| 13 Aug 19 | Joel Pereira | Loan | ||
| 13 Aug 19 | Joel Pereira | Loan | ||
| 12 Aug 19 | George Tanner | Loan | ||
| 08 Aug 19 | Romelu Lukaku | Undisclosed | ||
| 08 Aug 19 | Romelu Lukaku | Undisclosed | ||
| 05 Aug 19 | Harry Maguire | Undisclosed | ||
| 26 Jul 19 | Dean Henderson | Loan | ||
| 08 Jul 19 | Kieran O'Hara | Loan | ||
| 05 Jul 19 | Matthew Olosunde | Free | ||
| 04 Jul 19 | Ander Herrera | Free | ||
| 04 Jul 19 | Ander Herrera | Free | ||
| 03 Jul 19 | James Wilson | Free | ||
| 03 Jul 19 | James Wilson | Free | ||
| 01 Jul 19 | Antonio Valencia | Free | ||
| 29 Jun 19 | Aaron Wan-Bissaka | Undisclosed | ||
| 12 Jun 19 | Daniel James | Undisclosed | ||
| 12 Jun 19 | Daniel James | Undisclosed | ||
| 31 Jan 19 | Matthew Willock | Loan | ||
| 30 Jan 19 | Undisclosed | |||
| 18 Jan 19 | Regan Poole | Loan | ||
| 11 Jan 19 | Ethan Hamilton | Loan |
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