| 2026-10-22 | W. Grigg | Chesterfield → Forest Green | Free agent |
| 2026-10-21 | W. Grigg | Chesterfield → Forest Green | Free agent |
| 2026-09-27 | C. Dunkley | Chesterfield → Solihull Moors | Loan |
| 2026-09-02 | Luke Joseph Butterfield | Chesterfield → AFC Fylde | Loan |
| 2026-08-31 | K. Dyer | Chelsea → Chesterfield | Loan |
| 2026-08-31 | J. Randall | Bolton → Chesterfield | Loan |
| 2026-08-30 | L. Marsh | Sheffield Utd → Chesterfield | Loan |
| 2026-08-10 | P. Madden | Chesterfield → Bohemians | Free agent |
| 2026-07-29 | R. Lamptey | Millwall → Chesterfield | Loan |
| 2026-07-27 | F. Bryden | Crusaders FC → Chesterfield | Transfer |
| 2026-07-26 | F. Bryden | Crusaders FC → Chesterfield | Transfer |
| 2026-07-23 | L. Jessop | Chesterfield → Portadown | Free agent |
| 2026-07-21 | J. Grimes | Chesterfield → Boston United | Free agent |
| 2026-07-20 | J. Grimes | Chesterfield → Boston United | Free agent |
| 2026-07-16 | D. Anisjko | Nottingham Forest → Chesterfield | Free agent |
| 2026-07-16 | R. Hutton | Gillingham → Chesterfield | Free agent |
| 2026-07-15 | R. Hutton | Gillingham → Chesterfield | Free agent |
| 2026-07-09 | O. Wozniczka | Chesterfield → Chesterfield | - |
| 2026-07-08 | R. Sotiriou | Hapoel Katamon → Chesterfield | Free agent |
| 2026-07-08 | J. Koroma | Leyton Orient → Chesterfield | Loan |
| 2026-07-05 | V. Campbell | Chesterfield → Southend | Free agent |
| 2026-07-05 | A. Pond | Wolves → Chesterfield | Free agent |
| 2026-07-04 | V. Campbell | Chesterfield → Southend | Free agent |
| 2026-07-01 | A. Lewis | Chesterfield → AFC Fylde | Free agent |
| 2026-07-01 | J. Simpson | Leyton Orient → Chesterfield | Free agent |
| 2026-06-30 | A. Dobra | Chesterfield → Leyton Orient | Transfer |
| 2026-06-30 | B. Hobson | Chesterfield → Harrogate Town | Free agent |
| 2026-06-30 | A. Lewis | Chesterfield → AFC Fylde | Free agent |
| 2026-06-30 | J. Simpson | Leyton Orient → Chesterfield | Free agent |
| 2026-06-30 | G. McEachran | Grimsby → Chesterfield | Free agent |
| 2026-06-30 | J. Donacien | Chesterfield → Northampton | Free agent |
| 2026-06-29 | P. Madden | Chesterfield → Madden Patrick | Free agent |
| 2026-06-29 | P. Madden | Chesterfield → Bohemians | Free agent |
| 2026-06-29 | A. Dobra | Chesterfield → Leyton Orient | Transfer |
| 2026-06-29 | B. Hobson | Chesterfield → Harrogate Town | Free agent |
| 2026-06-29 | J. Grimes | Chesterfield → Grimes Jamie | Free agent |
| 2026-06-29 | J. Grimes | Chesterfield → Boston United | Free agent |
| 2026-06-29 | L. Jessop | Chesterfield → Jessop Liam | Free agent |
| 2026-06-29 | L. Jessop | Chesterfield → Portadown | Free agent |
| 2026-06-29 | F. Ladapo | Chesterfield → Ladapo Freddie | Free agent |
| 2026-06-29 | A. Rinaldo | Chesterfield → Rinaldo Ashton | Free agent |
| 2026-06-29 | R. Sotiriou | Hapoel Katamon → Chesterfield | Free agent |
| 2026-06-29 | G. McEachran | Grimsby → Chesterfield | Free agent |
| 2026-06-29 | J. Donacien | Chesterfield → Northampton | Free agent |
| 2026-06-29 | J. Fleck | Chesterfield → Fleck John | Free agent |
| 2026-05-30 | P. Madden | Accrington ST → Chesterfield | Return from loan |
| 2026-05-30 | J. Grimes | Boston United → Chesterfield | Return from loan |
| 2026-05-30 | J. Berry-McNally | Chesterfield → Wycombe | Return from loan |
| 2026-05-30 | L. Jessop | Lincoln Red Imps FC → Chesterfield | Return from loan |
| 2026-05-30 | S. Swinkels | Chesterfield → Aston Villa | Return from loan |
| 2026-05-30 | A. Lewis | AFC Fylde → Chesterfield | Return from loan |
| 2026-05-30 | Luke Joseph Butterfield | Accrington ST → Chesterfield | Return from loan |
| 2026-05-30 | S. Curtis | Chesterfield → Sheffield Utd | Return from loan |
| 2026-05-30 | S. Braybrooke | Chesterfield → Leicester | Return from loan |
| 2026-03-09 | A. Lewis | Chesterfield → AFC Fylde | Loan |
| 2026-02-04 | J. Grimes | Chesterfield → Boston United | Loan |
| 2026-01-21 | Luke Joseph Butterfield | Chesterfield → Accrington ST | Loan |
| 2026-01-19 | R. Darcy | Chesterfield → Wigan | Return from loan |
| 2026-01-15 | William Dickson | Manchester City → Chesterfield | Transfer |
| 2026-01-15 | R. Darcy | Chesterfield → Wigan | Return from loan |
| 2026-01-08 | T. Pearce | CF Montreal → Chesterfield | Free agent |
| 2026-01-06 | Devan Austin Tanton Pedraza | Chesterfield → Fulham | Return from loan |
| 2026-01-06 | M. Dibley-Dias | Chesterfield → Fulham | Return from loan |
| 2026-01-04 | William Dickson | Chesterfield → Manchester City (U23) | Return from loan |
| 2026-01-04 | William Dickson | Chesterfield → Manchester City | Return from loan |
| 2026-01-03 | S. Swinkels | Aston Villa → Chesterfield | Loan |
| 2026-01-03 | S. Curtis | Sheffield Utd → Chesterfield | Loan |
| 2026-01-03 | S. Braybrooke | Leicester → Chesterfield | Loan |
| 2026-01-01 | S. Swinkels | Exeter City → Chesterfield | Loan |