Chesterfield: every transfer in and out, fees paid and earned, squad market value and €330k earned.
| Date | Player | From | To | Fee |
|---|---|---|---|---|
| 2026-07-01 | Liam Jessop | Chesterfield | Without Club | — |
| 2026-01-22 | Luke Butterfield | Chesterfield | Accrington | Loan |
| 2026-01-04 | Sil Swinkels | Aston Villa U21 | Chesterfield | Loan |
| 2026-01-04 | Sam Curtis | Sheff Utd | Chesterfield | Loan |
| 2025-09-03 | Liam Jessop | Chesterfield | Lincoln FC | Loan |
| 2025-07-18 | Luke Butterfield | Everton U21 | Chesterfield | Free |
| 2025-07-01 | Zach Hemming | Boro U21 | Chesterfield | — |
| 2025-07-01 | Lee Bonis | ADO Den Haag | Chesterfield | — |
| 2025-01-31 | Liam Jessop | Chesterfield | Worksop | Loan |
| 2024-08-30 | Jenson Metcalfe | Everton U21 | Chesterfield | Loan |
| 2024-07-01 | Liam Jessop | Chesterf. U18 | Chesterfield | — |
| 2023-08-30 | Miguel Freckleton | Sheff Utd U21 | Chesterfield | Loan |
| 2023-03-06 | Andy Dallas | Solihull Moors | Chesterfield FC | Loan |
| 2022-10-13 | Calvin Miller | Chesterfield | Without Club | — |
| 2021-07-01 | Calvin Miller | Harrogate Town | Chesterfield | Free |
| 2019-11-21 | Liam Shaw | Sheff Wed U21 | Chesterfield FC | Loan |
| 2018-01-31 | Jacob Brown | Barnsley FC | Chesterfield FC | Loan |
| 2018-01-05 | Aaron Ramsdale | Bournemouth | Chesterfield | Loan |
| 2017-08-31 | Paul McGinn | Chesterfield | Partick Thistle | Free |
| 2017-07-01 | Jay O'Shea | Chesterfield | Bury | Free |