Stadium: Holker Street Round: 45
Referee: Martin Coy Home Manager: Robert Anthony Kelly Away Manager: Philip Brown
| England League 2 | 2021/01/09 15:00 | Southend v Barrow | L | 1-0 |
| England League 2 | 2021/01/16 15:00 | Barrow v Scunthorpe | W | 1-0 |
| England League 2 | 2021/01/09 15:00 | Southend v Barrow | L | 1-0 |
| England League 2 | 2020/12/29 19:45 | Barrow v Tranmere | D | 1-1 |
| England League 2 | 2020/12/26 15:00 | Port Vale v Barrow | W | 0-2 |
| England League 2 | 2020/12/19 15:00 | Barrow v Cheltenham | W | 3-0 |
| England League 2 | 2020/12/15 19:00 | Scunthorpe v Barrow | L | 2-1 |
| England League 2 | 2020/12/12 15:00 | Crawley Town v Barrow | L | 4-2 |
| England League 2 | 2020/12/05 15:00 | Barrow v Salford City | L | 0-1 |
| 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 |
| England League 2 | 2020/12/29 19:00 | Leyton Orient v Southend | L | 2-0 |
| England League 2 | 2020/12/26 13:00 | Southend v Colchester | W | 2-0 |
| England League 2 | 2020/12/19 15:00 | Mansfield v Southend | D | 1-1 |