Home History
| 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 |
| England League 2 | 2014/08/09 14:00 | Bury v Cheltenham | W | 0-1 |
| Club Friendly List | 2014/08/05 18:45 | Redditch v Cheltenham | D | 2-2 |
| Club Friendly List | 2014/08/02 14:00 | Kidderminster v Cheltenham | L | 3-0 |
Away History
| England League 2 | 2014/08/30 14:00 | Portsmouth v Newport County | L | 0-1 |
| England EFL Cup | 2014/08/27 18:45 | Stoke v Portsmouth | L | 3-0 |
| England League 2 | 2014/08/23 14:00 | Oxford Utd v Portsmouth | W | 0-1 |
| England League 2 | 2014/08/19 18:45 | Portsmouth v Northampton | W | 2-0 |
| England League 2 | 2014/08/16 14:00 | Portsmouth v Cambridge Utd | W | 2-1 |
| England EFL Cup | 2014/08/12 18:45 | Portsmouth v Peterborough | W | 1-0 |
| England League 2 | 2014/08/09 14:00 | Exeter v Portsmouth | D | 1-1 |
| Club Friendly List | 2014/08/02 14:00 | Portsmouth v Charlton | L | 1-2 |