| England FA Cup Qualification | 2020/11/04 19:45 | Stockport v Chesterfield | W | 4-0 |
| England National League | 2020/10/17 16:20 | Chesterfield v Stockport | W | 1-2 |
| England National League | 2019/08/26 14:00 | Stockport v Chesterfield | W | 2-0 |
| England National League | 2021/02/13 15:00 | Stockport v Aldershot | D | 0-0 |
| England National League | 2021/02/06 17:30 | Stockport v Yeovil | W | 1-0 |
| England National League | 2021/02/02 19:00 | Stockport v Sutton Utd | L | 0-2 |
| England National League | 2021/01/30 15:00 | Woking v Stockport | W | 1-4 |
| England National League | 2021/01/23 15:00 | Stockport v Boreham Wood | D | 1-1 |
| England National League | 2021/01/19 19:00 | Dag & Red v Stockport | W | 0-2 |
| England FA Trophy | 2021/01/16 15:00 | Stockport v Notts County | L | 1-2 |
| England FA Cup | 2021/01/11 20:00 | Stockport v West Ham | L | 0-1 |
| England National League | 2021/01/30 15:00 | Dag & Red v Chesterfield | D | 2-2 |
| England National League | 2021/01/26 19:45 | Boreham Wood v Chesterfield | D | 0-0 |
| England National League | 2021/01/23 15:00 | Chesterfield v Wrexham | W | 2-1 |
| England FA Trophy | 2021/01/20 19:45 | Boston Utd v Chesterfield | W | 2-5 |
| England National League | 2021/01/05 19:45 | Solihull Moors v Chesterfield | L | 2-1 |
| England National League | 2021/01/02 15:00 | Chesterfield v Solihull Moors | W | 1-0 |
| England FA Trophy | 2020/12/19 15:00 | Chesterfield v Brackley | W | 4-3 |
| England National League | 2020/12/12 15:00 | Chesterfield v Barnet | W | 6-0 |