Head to Head
| England League 1 | 2017/04/04 18:45 | Southend v Bolton | W | 0-1 |
| England League 1 | 2016/09/03 14:00 | Bolton v Southend | D | 1-1 |
Home History
| England League 1 | 2019/10/22 18:45 | Bristol Rovers v Bolton | W | 0-2 |
| England League 1 | 2019/10/19 14:00 | Bolton v Rochdale | L | 1-3 |
| England League 1 | 2019/10/07 19:00 | Bolton v Blackpool | D | 0-0 |
| England EFL Trophy | 2019/10/01 18:45 | Rochdale v Bolton | L | 6-4 |
| England League 1 | 2019/09/28 14:00 | Portsmouth v Bolton | L | 1-0 |
| England League 1 | 2019/09/21 14:00 | Bolton v Sunderland | D | 1-1 |
| England League 1 | 2019/09/17 19:00 | Bolton v Oxford Utd | D | 0-0 |
| England League 1 | 2019/09/14 14:00 | Rotherham v Bolton | L | 6-1 |
Away History
| England League 1 | 2019/10/26 14:00 | Southend v Ipswich | L | 1-3 |
| England League 1 | 2019/10/22 18:45 | Southend v Doncaster | L | 1-7 |
| England League 1 | 2019/10/18 18:45 | Tranmere v Southend | D | 1-1 |
| England League 1 | 2019/10/12 14:00 | Southend v AFC Wimbledon | L | 1-4 |
| England League 1 | 2019/10/05 14:00 | Gillingham v Southend | L | 3-1 |
| England EFL Trophy | 2019/10/01 18:45 | Southend v Brighton U21 | L | 0-2 |
| England League 1 | 2019/09/28 14:00 | Southend v Accrington Stanley | L | 0-1 |
| England League 1 | 2019/09/21 14:00 | Milton Keynes Dons v Southend | W | 0-1 |