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 | 2019/12/14 15:00 | Peterborough v Bolton | L | 1-0 |
| England EFL Trophy | 2019/12/10 19:45 | Accrington Stanley v Bolton | L | 2-0 |
| England League 1 | 2019/12/07 15:00 | Bolton v AFC Wimbledon | D | 2-2 |
| England League 1 | 2019/11/23 15:00 | Accrington Stanley v Bolton | L | 7-1 |
| England League 1 | 2019/11/16 15:00 | Bolton v Milton Keynes Dons | W | 1-0 |
| England FA Cup | 2019/11/09 15:00 | Bolton v Plymouth | L | 0-1 |
| England League 1 | 2019/11/02 15:00 | Bolton v Fleetwood Town | W | 2-1 |
| England EFL Trophy | 2019/10/29 19:00 | Bolton v Man City U21 | W | 3-1 |
Away History
| England League 1 | 2019/12/14 15:00 | Southend v Rotherham | D | 2-2 |
| England League 1 | 2019/12/07 15:00 | Bristol Rovers v Southend | L | 4-2 |
| England League 1 | 2019/12/03 19:45 | Burton Albion v Southend | D | 1-1 |
| England League 1 | 2019/11/23 15:00 | Southend v Oxford Utd | L | 0-4 |
| England EFL Trophy | 2019/11/13 19:45 | Southend v AFC Wimbledon | W | 3-1 |
| England FA Cup | 2019/11/10 12:00 | Dover v Southend | L | 1-0 |
| England League 1 | 2019/11/05 19:45 | Portsmouth v Southend | L | 4-1 |
| England League 1 | 2019/11/02 15:00 | Sunderland v Southend | L | 1-0 |