Home History
| Club Friendly List | 2019/07/08 18:45 | Wimborne Town v Weymouth | W | 2-3 |
| UK Friendlies | 2019/07/02 18:45 | Hamworthy Utd v Weymouth | W | 1-3 |
| England Southern Premier League South | 2019/04/27 14:00 | Weymouth v Farnborough | W | 3-0 |
| England Southern Premier League South | 2019/04/22 14:00 | Poole Town v Weymouth | D | 1-1 |
| England Southern Premier League South | 2019/04/20 14:00 | Weymouth v Chesham | D | 1-1 |
| England Southern Premier League South | 2019/04/13 14:00 | Beaconsfield v Weymouth | L | 1-0 |
| England Southern Premier League South | 2019/04/06 14:00 | Weymouth v Staines Town | W | 4-0 |
| England Southern Premier League South | 2019/04/02 18:45 | Weymouth v Met Police | W | 4-0 |
Away History
| Club Friendly List | 2019/07/09 18:45 | Billericay Town v Southend | W | 2-3 |
| England League 1 | 2019/05/04 16:30 | Southend v Sunderland | W | 2-1 |
| England League 1 | 2019/04/27 14:00 | Rochdale v Southend | L | 1-0 |
| England League 1 | 2019/04/22 12:00 | Southend v Burton Albion | W | 3-2 |
| England League 1 | 2019/04/19 14:00 | Walsall v Southend | D | 1-1 |
| England League 1 | 2019/04/13 14:00 | Southend v Wycombe | L | 0-2 |
| England League 1 | 2019/04/06 14:00 | Fleetwood Town v Southend | D | 2-2 |
| England League 1 | 2019/03/30 15:00 | Southend v Shrewsbury | L | 0-2 |