| P | # | Player | Born | Height | Weight | Contract | |
|---|---|---|---|---|---|---|---|
| GK | Ole Söderberg | 1990-07-20 | 194 | 94 | 2021-12-31 | ||
| D | James Hurst | 1992-01-31 | 173 | 75 | |||
| D | Tendayi Darikwa | 1991-12-13 | 187 | 77 | 2021-06-30 | ||
| F | Jordan Bowery | 1991-07-02 | 185 | 76 | 2015 jun |
| Date | Player | From | To | Status | Src |
|---|---|---|---|---|---|
| 30.Jun | Jamal Campbell-Ryce (M) | Chesterfield FC | Sheffield United | Confirmed | |
| 21.Mar | Jamal Campbell-Ryce (M) | Sheffield United | Chesterfield FC | Confirmed | |
| 18.Sep | Chris Herd (M) | Aston Villa FC | Chesterfield FC | Confirmed | |
| 25.Aug | Liam O'Neil (D) | West Bromwich Albion | Chesterfield FC | Confirmed | |
| 14.Aug | Liam Cooper (D) | Chesterfield FC | Leeds United | Confirmed | |
| 24.Nov | Scott Griffiths (D) | Peterborough United | Chesterfield FC | Confirmed | |
| 8.Nov | Temitope Obadeyi (F) | Bolton Wanderers | Chesterfield FC | Confirmed | |
| 9.Nov | Dan Gray (D) | Chesterfield FC | Macclesfield Town | Confirmed | |
| 3.Nov | Dean Holden (D) | Chesterfield FC | Rochdale AFC | Confirmed | |
| 3.Nov | Neal Trotman (D) | Rochdale AFC | Chesterfield FC | Confirmed |