Home History
| 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 |
| England National League | 2020/02/01 17:20 | Notts County v Chesterfield | L | 3-0 |
Away History
| Club Friendly List | 2020/09/15 18:45 | Guiseley v Stockport | L | 1-5 |
| Europe Friendlies | 2020/09/12 12:00 | Guiseley v Halifax | L | 1-2 |
| Club Friendly List | 2020/09/08 18:30 | Mickleover Sports v Guiseley | D | 1-1 |
| Club Friendly List | 2020/09/01 18:30 | Worksop v Guiseley | D | 0-0 |
| UK Friendlies | 2020/08/29 13:59 | Thackley v Guiseley | W | 0-1 |
| England National League North | 2020/03/14 15:00 | Kings Lynn Town v Guiseley | W | 0-1 |
| England County Cup | 2020/03/09 19:45 | Harrogate Town v Guiseley | W | 1-2 |
| England National League North | 2020/03/07 15:00 | Guiseley v Leamington | W | 3-0 |
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