Home History
| England League 2 | 2014/09/13 14:00 | Luton v Cheltenham | L | 1-0 |
| England League 2 | 2014/09/06 14:00 | Morecambe v Cheltenham | D | 0-0 |
| England EFL Trophy | 2014/09/02 18:45 | Cheltenham v Oxford Utd | W | 2-0 |
| England League 2 | 2014/08/30 14:00 | Cheltenham v Hartlepool | W | 1-0 |
| England League 2 | 2014/08/23 14:00 | Tranmere v Cheltenham | W | 2-3 |
| England League 2 | 2014/08/19 18:45 | Cheltenham v Carlisle | D | 0-0 |
| England League 2 | 2014/08/16 14:00 | Cheltenham v Accrington Stanley | W | 2-1 |
| England EFL Cup | 2014/08/12 18:45 | Brighton v Cheltenham | L | 2-0 |
Away History
| England League 2 | 2014/09/13 14:00 | Southend v Portsmouth | W | 2-0 |
| England League 2 | 2014/09/06 14:00 | Southend v Oxford Utd | D | 1-1 |
| England EFL Trophy | 2014/09/02 18:45 | AFC Wimbledon v Southend | L | 6-4 |
| England League 2 | 2014/08/30 14:00 | Plymouth v Southend | L | 2-0 |
| England League 2 | 2014/08/23 14:00 | Carlisle v Southend | D | 1-1 |
| England League 2 | 2014/08/19 18:45 | Southend v AFC Wimbledon | L | 0-1 |
| England League 2 | 2014/08/16 14:00 | Southend v Stevenage | W | 2-0 |
| England EFL Cup | 2014/08/12 18:45 | Southend v Walsall | L | 1-2 |