| England FA Cup Qualification | 2023/10/14 14:00 | Yeovil v Southend | L | 2-0 |
| England National League | 2023/10/07 14:00 | Woking v Southend | W | 0-2 |
| England National League | 2023/10/03 18:45 | Southend v Oxford City | W | 2-0 |
| England National League | 2023/09/30 14:00 | Rochdale v Southend | D | 2-2 |
| England National League | 2023/09/26 18:45 | Aldershot v Southend | D | 1-1 |
| England National League | 2023/09/23 14:00 | Southend v AFC Fylde | L | 1-2 |
| England National League | 2023/09/19 18:45 | Southend v Maidenhead Utd | W | 2-0 |
| England National League | 2023/09/16 14:00 | York v Southend | L | 3-0 |
| England National League South | 2023/10/14 14:00 | Hampton & Richmond v Dartford | W | 4-3 |
| England National League South | 2023/10/07 14:00 | Havant and W v Hampton & Richmond | W | 1-2 |
| England FA Cup Qualification | 2023/09/30 14:00 | Lewes v Hampton & Richmond | L | 3-0 |
| England National League South | 2023/09/23 14:00 | Hampton & Richmond v Yeovil | L | 1-2 |
| England FA Cup Qualification | 2023/09/16 14:00 | Southall v Hampton & Richmond | W | 1-2 |
| England National League South | 2023/09/09 14:00 | Weston Super Mare v Hampton & Richmond | D | 1-1 |
| England National League South | 2023/09/05 18:45 | Hampton & Richmond v Weymouth | W | 1-0 |
| England National League South | 2023/09/02 14:00 | Farnborough v Hampton & Richmond | L | 3-1 |