Home History
| Club Friendly List | 2020/09/15 18:45 | St Albans v Wealdstone | L | 4-0 |
| UK Friendlies | 2020/09/01 18:45 | Northwood v Wealdstone | W | 0-6 |
| Club Friendly List | 2020/08/25 18:00 | Wealdstone v Luton | L | 0-3 |
| UK Friendlies | 2020/08/22 10:30 | Bedford Town v Wealdstone | W | 1-3 |
| England National League South | 2020/03/14 15:00 | Chippenham Town v Wealdstone | D | 1-1 |
| England National League South | 2020/03/07 15:00 | Wealdstone v Dulwich | W | 2-1 |
| England National League South | 2020/02/29 15:00 | Dartford v Wealdstone | D | 0-0 |
| England National League South | 2020/02/25 19:45 | Wealdstone v Chelmsford | L | 0-1 |
Away History
| UK Friendlies | 2020/09/26 11:00 | Chesterfield v Guiseley | L | 0-1 |
| Club Friendly List | 2020/09/19 11:00 | Alfreton Town v Chesterfield | L | 2-0 |
| Club Friendly List | 2020/09/08 18:30 | Belper Town v Chesterfield | W | 2-3 |
| England National League | 2020/03/14 15:00 | Dover v Chesterfield | D | 1-1 |
| England National League | 2020/03/07 15:00 | Chorley v Chesterfield | W | 1-2 |
| England National League | 2020/03/03 19:45 | Chesterfield v Harrogate Town | L | 3-4 |
| England National League | 2020/02/22 15:00 | Chesterfield v Ebbsfleet United | W | 4-0 |
| England National League | 2020/02/08 13:00 | Chesterfield v Wrexham | W | 3-2 |