Home History
| England National League | 2019/08/10 14:00 | Yeovil v Stockport | D | 1-1 |
| England National League | 2019/08/06 18:45 | Notts County v Stockport | D | 1-1 |
| England National League | 2019/08/03 11:30 | Stockport v Maidenhead Utd | L | 0-1 |
| Club Friendly List | 2019/07/27 14:00 | Oldham v Stockport | W | 0-2 |
| Club Friendly List | 2019/07/23 18:45 | Altrincham v Stockport | W | 1-2 |
| Club Friendly List | 2019/07/20 14:00 | Guiseley v Stockport | D | 2-2 |
| Club Friendly List | 2019/07/13 14:00 | Curzon Ashton v Stockport | W | 0-2 |
| UK Friendlies | 2019/07/09 18:44 | Stockport Town FC v Stockport | W | 0-10 |
Away History
| England National League | 2019/08/10 14:00 | Boreham Wood v Chesterfield | D | 2-2 |
| England National League | 2019/08/06 18:45 | Maidenhead Utd v Chesterfield | D | 1-1 |
| England National League | 2019/08/03 14:00 | Chesterfield v Dover | L | 1-2 |
| Club Friendly List | 2019/07/27 14:00 | Chesterfield v Burton Albion | L | 2-5 |
| Club Friendly List | 2019/07/24 18:30 | Sheffield FC v Chesterfield | L | 2-1 |
| Elite Club Friendlies | 2019/07/23 18:30 | Chesterfield v Sheff Utd | L | 0-5 |
| Club Friendly List | 2019/07/20 14:00 | Chesterfield v Rotherham | L | 1-2 |
| Club Friendly List | 2019/07/16 18:30 | Matlock Town v Chesterfield | W | 1-2 |