Home History
| England National League South | 2023/10/07 14:00 | Weston Super Mare v Chelmsford | W | 0-3 |
| England FA Cup Qualification | 2023/10/02 18:30 | Chelmsford v Bromsgrove | W | 3-0 |
| England FA Cup Qualification | 2023/09/30 14:00 | Bromsgrove v Chelmsford | D | 2-2 |
| England National League South | 2023/09/23 14:00 | Chelmsford v St Albans | L | 0-2 |
| England FA Cup Qualification | 2023/09/18 18:30 | Chelmsford v Ware | W | 2-1 |
| England FA Cup Qualification | 2023/09/16 14:00 | Ware v Chelmsford | D | 3-3 |
| England National League South | 2023/09/09 14:00 | Torquay v Chelmsford | L | 2-1 |
| England National League South | 2023/09/04 18:45 | Chelmsford v Hemel Hempstead | L | 1-2 |
Away History
| England FA Trophy | 2023/10/07 14:00 | Radcliffe FC v Whitby | L | 3-2 |
| England FA Cup Qualification | 2023/09/30 14:00 | Whitby v Morpeth Town | W | 1-0 |
| England Northern Premier League | 2023/09/26 18:45 | Whitby v Marske United | W | 4-2 |
| England Northern Premier League | 2023/09/23 14:00 | FC United of Manchester v Whitby | D | 1-1 |
| England FA Cup Qualification | 2023/09/16 14:00 | Whitby v Prescot Cables | W | 2-1 |
| England Northern Premier League | 2023/09/09 14:00 | Whitby v Warrington Rylands | L | 1-3 |
| England FA Cup Qualification | 2023/09/01 18:45 | Goole v Whitby | W | 0-6 |
| England Northern Premier League | 2023/08/28 14:00 | Ilkeston v Whitby | W | 2-4 |