Home History
| England National League | 2023/09/30 14:00 | Maidenhead Utd v Chesterfield | D | 1-1 |
| England National League | 2023/09/26 19:00 | Rochdale v Chesterfield | W | 1-2 |
| England National League | 2023/09/23 14:00 | Chesterfield v Wealdstone | W | 3-2 |
| England National League | 2023/09/19 18:45 | Chesterfield v Halifax | W | 3-2 |
| England National League | 2023/09/16 14:00 | Ebbsfleet United v Chesterfield | W | 0-1 |
| England National League | 2023/09/09 14:00 | Chesterfield v Dag & Red | W | 3-1 |
| England National League | 2023/09/02 14:00 | Aldershot v Chesterfield | W | 3-4 |
| England National League | 2023/08/28 14:00 | Chesterfield v Hartlepool | W | 3-2 |
Away History
| England National League North | 2023/09/23 14:00 | Southport v Tamworth | D | 0-0 |
| England FA Cup Qualification | 2023/09/16 14:00 | Morpeth Town v Southport | L | 3-0 |
| England National League North | 2023/09/09 14:00 | Kings Lynn Town v Southport | W | 1-4 |
| England National League North | 2023/09/05 18:45 | Southport v Scarborough Athletic | W | 3-1 |
| England National League North | 2023/09/02 14:00 | Hereford FC v Southport | W | 0-1 |
| England National League North | 2023/08/28 14:00 | Southport v Chorley | L | 0-2 |
| England National League North | 2023/08/26 14:00 | Brackley v Southport | D | 0-0 |
| England National League North | 2023/08/19 14:00 | Southport v Boston Utd | L | 0-2 |
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