| Club Friendly List | 2018/07/14 14:00 | Boston Utd v Chesterfield | D | 1-1 |
| England National League North | 2020/08/01 14:00 | Boston Utd v Altrincham | L | 0-1 |
| England National League North | 2020/07/25 16:30 | Boston Utd v Gateshead | W | 5-3 |
| England County Cup | 2020/03/10 19:44 | Cleethorpes Town v Boston Utd | L | 1-0 |
| England National League North | 2020/03/07 15:00 | Curzon Ashton v Boston Utd | D | 1-1 |
| England National League North | 2020/03/03 19:45 | Brackley v Boston Utd | D | 0-0 |
| England National League North | 2020/02/25 19:45 | Boston Utd v Gateshead | L | 0-3 |
| England National League North | 2020/02/22 15:00 | Boston Utd v AFC Telford | W | 1-0 |
| England National League North | 2020/02/08 15:00 | Boston Utd v York | W | 3-1 |
| 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 |
| England National League | 2020/01/25 15:00 | Chesterfield v AFC Fylde | D | 1-1 |
| England National League | 2020/01/18 15:00 | Eastleigh v Chesterfield | W | 0-2 |