| FA Cup | M. | W | D | L | goals | |||
| at home | 1 | 1 | 0 | 0 | 1 | : | 0 | |
| Away | 1 | 0 | 0 | 1 | 0 | : | 3 | |
| ∑ | 2 | 1 | 0 | 1 | 1 | : | 3 | |
| League Cup | M. | W | D | L | goals | |||
| Away | 1 | 1 | 0 | 0 | 1 | : | 0 | |
| ∑ | 1 | 1 | 0 | 0 | 1 | : | 0 | |
| League Two | M. | W | D | L | goals | |||
| at home | 1 | 0 | 1 | 0 | 0 | : | 0 | |
| Away | 1 | 1 | 0 | 0 | 2 | : | 0 | |
| ∑ | 2 | 1 | 1 | 0 | 2 | : | 0 | |
| overall | M. | W | D | L | goals | |||
| at home | 2 | 1 | 1 | 0 | 1 | : | 0 | |
| Away | 3 | 2 | 0 | 1 | 3 | : | 3 | |
| Neutral Place | 0 | 0 | 0 | 0 | 0 | : | 0 | |
| ∑ | 5 | 3 | 1 | 1 | 4 | : | 3 | |
| FA Cup | |||||
| 2023/2024 | 1. Round | Chesterfield FC | - | Portsmouth FC | 1:0 (1:0) |
| 1968/1969 | 3. Round | Portsmouth FC | - | Chesterfield FC | 3:0 |
| League Cup | |||||
| 1972/1973 | 2. Round | Portsmouth FC | - | Chesterfield FC | 0:1 |
| League Two | |||||
| 2013/2014 | 34. Round | Chesterfield FC | - | Portsmouth FC | 0:0 (0:0) |
| 2013/2014 | 5. Round | Portsmouth FC | - | Chesterfield FC | 0:2 (0:0) |
|
For games that were decided on penalties the score after 120 minutes will be included in the ranking |
England ![Chesterfield FC [U18]](https://s.hs-data.com/bilder/wappen/mini/28245.gif?fallback=png "Chesterfield FC [U18]"){kind=small}