Head to Head
| England - League 2 | 2020/11/28 15:00 | Bolton v Southend | L | 3-0 |
| England - League 1 | 2019/12/21 15:00 | Bolton v Southend | L | 3-2 |
| England - League 1 | 2017/04/04 18:45 | Southend v Bolton | L | 0-1 |
| England - League 1 | 2016/09/03 14:00 | Bolton v Southend | D | 1-1 |
Home History
| England - League 2 | 2021/02/13 15:00 | Cambridge Utd v Southend | D | 0-0 |
| England - League 2 | 2021/02/09 19:00 | Newport County v Southend | W | 0-1 |
| England - League 2 | 2021/01/30 15:00 | Port Vale v Southend | L | 5-1 |
| England - League 2 | 2021/01/26 19:00 | Southend v Bradford | L | 1-3 |
| England - League 2 | 2021/01/23 15:00 | Southend v Mansfield | L | 0-1 |
| England - League 2 | 2021/01/19 19:00 | Southend v Cambridge Utd | L | 1-2 |
| England - League 2 | 2021/01/16 15:00 | Grimsby v Southend | D | 0-0 |
| England - League 2 | 2021/01/09 15:00 | Southend v Barrow | W | 1-0 |
Away History
| England - League 2 | 2021/02/17 17:00 | Mansfield v Bolton | W | 2-3 |
| England - League 2 | 2021/02/13 15:00 | Bolton v Stevenage | W | 1-0 |
| England - League 2 | 2021/02/09 19:00 | Bolton v Morecambe | D | 1-1 |
| England - League 2 | 2021/01/30 15:00 | Bolton v Leyton Orient | W | 2-0 |
| England - League 2 | 2021/01/23 15:00 | Tranmere v Bolton | L | 2-1 |
| England - League 2 | 2021/01/16 15:00 | Bolton v Cheltenham | D | 1-1 |
| England - League 2 | 2021/01/12 19:00 | Exeter v Bolton | D | 1-1 |
| England - League 2 | 2021/01/02 15:00 | Bolton v Crawley Town | L | 0-1 |