Home History
| England FA Cup | 2023/12/03 14:00 | Chesterfield v Leyton Orient | W | 1-0 |
| England National League | 2023/11/25 15:00 | Chesterfield v Eastleigh | W | 3-2 |
| England National League | 2023/11/21 19:45 | Woking v Chesterfield | W | 0-2 |
| England National League | 2023/11/18 15:00 | Southend v Chesterfield | L | 2-1 |
| England National League | 2023/11/11 15:00 | Chesterfield v Barnet | W | 4-2 |
| England FA Cup | 2023/11/05 12:15 | Chesterfield v Portsmouth | W | 1-0 |
| England National League | 2023/10/28 14:00 | Kidderminster v Chesterfield | W | 1-3 |
| England National League | 2023/10/24 18:45 | Chesterfield v York | W | 4-0 |
Away History
| England National League North | 2023/11/25 15:00 | Buxton v Southport | W | 0-1 |
| England National League North | 2023/11/21 19:45 | Scunthorpe v Southport | L | 1-0 |
| England FA Trophy | 2023/11/18 15:00 | Southport v South Shields | W | 4-0 |
| England National League North | 2023/11/14 19:45 | Southport v Farsley Celtic | D | 1-1 |
| England National League North | 2023/11/11 15:00 | Southport v South Shields | W | 1-0 |
| England National League North | 2023/11/07 19:45 | Blyth Spartans v Southport | D | 3-3 |
| England National League North | 2023/11/04 15:00 | Rushall Olympic v Southport | W | 2-3 |
| England National League North | 2023/10/28 14:00 | Southport v Banbury | L | 0-1 |