| 6 Dec 2025 | FA Cup | Chesterfield - Doncaster Rovers | H | Chesterfield | €0.30m | €0.21m |
| 1 Nov 2025 | FA Cup | Stevenage - Chesterfield | A | Stevenage | €0.10m | €0.05m |
| 30 Nov 2024 | FA Cup | Exeter City - Chesterfield | A | Exeter | €0.23m | €0.06m |
| 2 Nov 2024 | FA Cup | Chesterfield - Horsham | H | Chesterfield | €0.24m | €0.16m |
| 6 Jan 2024 | FA Cup | Watford - Chesterfield | A | Watford | €0.85m | €0.07m |
| 3 Dec 2023 | FA Cup | Chesterfield - Leyton Orient | H | Chesterfield | €0.40m | €0.31m |
| 5 Nov 2023 | FA Cup | Chesterfield - Portsmouth | H | Chesterfield | €0.41m | €0.31m |
| 17 Jan 2023 | FA Cup | West Bromwich Albion - Chesterfield | A | West Bromwich | €0.67m | €0.07m |
| 7 Jan 2023 | FA Cup | Chesterfield - West Bromwich Albion | H | Chesterfield | €0.48m | €0.38m |
| 26 Nov 2022 | FA Cup | AFC Wimbledon - Chesterfield | A | London | €0.34m | €0.14m |
| 5 Nov 2022 | FA Cup | Chesterfield - Northampton Town | H | Chesterfield | €0.29m | €0.20m |
| 8 Jan 2022 | FA Cup | Chelsea - Chesterfield | A | London | €3.2m | €0.14m |
| 5 Dec 2021 | FA Cup | Salford City - Chesterfield | A | Salford | €0.10m | €0.04m |
| 6 Nov 2021 | FA Cup | Chesterfield - Southend United | H | Chesterfield | €0.23m | €0.15m |
| 2 Dec 2018 | FA Cup | Chesterfield - Grimsby Town | H | Chesterfield | €0.22m | €0.14m |
| 20 Nov 2018 | FA Cup | Billericay Town - Chesterfield | A | — | €0.12m | €0.05m |
| 10 Nov 2018 | FA Cup | Chesterfield - Billericay Town | H | Chesterfield | €0.14m | €0.07m |
| 4 Nov 2017 | FA Cup | Bradford City - Chesterfield | A | Bradford | €0.23m | €0.06m |
| 3 Dec 2016 | FA Cup | Chesterfield - Wycombe Wanderers | H | Chesterfield | €0.18m | €0.10m |
| 5 Nov 2016 | FA Cup | Colchester United - Chesterfield | A | Colchester | €0.09m | €0.04m |