Chesterfield (League Two): every transfer in and out, fees paid and earned, squad market value.
| Date | Player | From | To | Fee |
|---|---|---|---|---|
| 2026-07-27 | Fraser Bryden | Crusaders | Chesterfield | Free |
| 2026-07-22 | Jamie Grimes | Chesterfield | Boston United | Free |
| 2026-07-17 | Danny Anijsko | Nottingham Forest U21 | Chesterfield | Free |
| 2026-07-17 | Remeao Hutton | Gillingham | Chesterfield | Free |
| 2026-07-09 | Josh Koroma | Leyton Orient | Chesterfield | Loan |
| 2026-07-09 | Ruel Sotiriou | Hapoel Jerusalem | Chesterfield | Free |
| 2026-07-06 | Alfie Pond | Wolves U21 | Chesterfield | Free |
| 2026-07-02 | Jack Simpson | Leyton Orient | Chesterfield | Free |
| 2026-07-02 | Adam Lewis | Chesterfield | Fylde | Free |
| 2026-07-01 | George McEachran | Grimsby Town | Chesterfield | Free |
| 2026-07-01 | Janoi Donacien | Chesterfield | Northampton Town | Free |
| 2026-07-01 | Armando Dobra | Chesterfield | Leyton Orient | Free |
| 2026-03-10 | Adam Lewis | Chesterfield | Fylde | Loan |
| 2026-02-05 | Jamie Grimes | Chesterfield | Boston United | Loan |
| 2026-01-16 | Will Dickson | Manchester City U21 | Chesterfield | Free |
| 2026-01-04 | Sammy Braybrooke | Leicester U21 | Chesterfield | Loan |
| 2026-01-04 | Sam Curtis | Sheffield United | Chesterfield | Loan |
| 2026-01-01 | Malik Owolabi-Belewu | Forge | Chesterfield | Free |
| 2025-09-03 | Liam Jessop | Chesterfield | Lincoln Red Imps | Loan |
| 2025-09-01 | Will Dickson | Manchester City U21 | Chesterfield | Loan |