Home History
| England - National League | 2020/10/31 15:00 | Stockport v Weymouth | W | 1-2 |
| England - National League | 2020/10/27 19:45 | Bromley v Weymouth | L | 3-2 |
| England - FA Cup - Qualifikation | 2020/10/24 14:00 | Weymouth v Oxford City | L | 2-3 |
| England - National League | 2020/10/17 14:00 | Weymouth v Kings Lynn Town | W | 2-1 |
| England - National League | 2020/10/13 18:45 | Barnet v Weymouth | L | 1-0 |
| England - National League | 2020/10/10 14:00 | Weymouth v Sutton Utd | L | 0-1 |
| England - National League | 2020/10/06 18:45 | Weymouth v Woking | L | 0-1 |
| England - National League | 2020/10/03 14:00 | Altrincham v Weymouth | D | 0-0 |
Away History
| England - National League | 2020/11/21 15:00 | Chesterfield v Notts County | L | 2-3 |
| England - National League | 2020/11/17 19:45 | Altrincham v Chesterfield | L | 3-2 |
| England - National League | 2020/11/14 15:00 | Chesterfield v Maidenhead Utd | L | 1-2 |
| England - FA Cup - Qualifikation | 2020/11/04 19:45 | Stockport v Chesterfield | L | 4-0 |
| England - National League | 2020/10/31 15:00 | Yeovil v Chesterfield | W | 0-1 |
| England - National League | 2020/10/20 18:45 | Wealdstone v Chesterfield | L | 3-2 |
| England - National League | 2020/10/17 16:20 | Chesterfield v Stockport | L | 1-2 |
| England - National League | 2020/10/13 18:45 | Torquay v Chesterfield | L | 2-1 |