Head to Head
| England League 1 | 2019/12/21 15:00 | Bolton v Southend | W | 3-2 |
| 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 2 | 2020/11/24 19:00 | Scunthorpe v Bolton | W | 0-1 |
| England League 2 | 2020/11/21 15:00 | Stevenage v Bolton | W | 1-2 |
| England EFL Trophy | 2020/11/17 19:00 | Bolton v Newcastle U21 | W | 3-2 |
| England League 2 | 2020/11/13 19:45 | Bolton v Salford City | W | 2-0 |
| England FA Cup | 2020/11/07 15:00 | Bolton v Crewe | L | 2-3 |
| England League 2 | 2020/11/03 19:00 | Bolton v Mansfield | D | 1-1 |
| England League 2 | 2020/10/31 15:00 | Leyton Orient v Bolton | L | 4-0 |
| England League 2 | 2020/10/27 19:00 | Bolton v Bradford | W | 1-0 |
Away History
| England League 2 | 2020/11/24 19:00 | Southend v Forest Green | L | 0-1 |
| England League 2 | 2020/11/14 15:00 | Walsall v Southend | W | 0-1 |
| England EFL Trophy | 2020/11/10 19:00 | Colchester v Southend | L | 6-1 |
| England FA Cup | 2020/11/07 15:00 | Boreham Wood v Southend | L | 7-6 |
| England League 2 | 2020/11/03 19:00 | Bradford v Southend | L | 3-0 |
| England League 2 | 2020/10/31 15:00 | Southend v Port Vale | L | 0-2 |
| England League 2 | 2020/10/27 19:00 | Southend v Oldham | L | 1-2 |
| England League 2 | 2020/10/24 14:00 | Tranmere v Southend | L | 2-0 |