Cheltenham: every transfer in and out, fees paid and earned, squad market value.
| Date | Player | From | To | Fee |
|---|---|---|---|---|
| 2025-10-10 | Jonathan Tomkinson | Without Club | Cheltenham | — |
| 2025-08-08 | George Harmon | Ross County | Cheltenham | Free |
| 2025-01-17 | Ethan Williams | Man Utd U21 | Cheltenham | Loan |
| 2025-01-01 | Ashley Hay | Brentford B | Cheltenham | Loan |
| 2024-08-02 | Joel Colwill | Cardiff U21 | Cheltenham | Loan |
| 2024-07-01 | Will Ferry | Cheltenham | Dundee United | Free |
| 2024-07-01 | Luke Southwood | Cheltenham | Bolton | Free |
| 2023-09-01 | Nathan Butler-Oyedeji | Arsenal U21 | Cheltenham | Loan |
| 2023-08-29 | Cameron Peupion | Brighton U21 | Cheltenham | Loan |
| 2023-07-11 | Luke Southwood | Reading | Cheltenham | Free |
| 2022-08-09 | Will Ferry | Southampton U21 | Cheltenham | — |
| 2022-07-22 | Luke Southwood | Reading | Cheltenham | Loan |
| 2022-07-04 | Dan Nlundulu | Southampton | Cheltenham | Loan |
| 2022-01-17 | Kyle Vassell | Cheltenham | San Diego Loyal | Free |
| 2022-01-17 | Kion Etete | Tottenham U23 | Cheltenham | Loan |
| 2022-01-11 | Aaron Ramsey | Aston Villa U23 | Cheltenham | Loan |
| 2022-01-06 | Dan Nlundulu | Southampton | Cheltenham | Loan |
| 2021-08-09 | Kyle Vassell | Rotherham | Cheltenham | Free |
| 2021-01-29 | Indiana Vassilev | Aston Villa U23 | Cheltenham | Loan |
| 2020-08-01 | Finn Azaz | West Brom U23 | Cheltenham | Loan |