[20] Gillingham 0-1 Portsmouth [9] 2021-08-01 07:00
Stadium: MEMS Priestfield Stadium Round: 20
Referee: Dean Whitestone Home Manager: Steve Evans Away Manager: Danny Cowley
Head to Head
| England League 1 | 2021/02/27 15:00 | Portsmouth v Gillingham | D | 1-1 |
| England League 1 | 2020/10/20 17:30 | Gillingham v Portsmouth | L | 0-2 |
| England League 1 | 2020/01/01 15:00 | Gillingham v Portsmouth | D | 1-1 |
| England League 1 | 2019/10/12 14:00 | Portsmouth v Gillingham | D | 0-0 |
| England League 1 | 2018/12/26 13:00 | Gillingham v Portsmouth | W | 2-0 |
| England League 1 | 2018/10/06 14:00 | Portsmouth v Gillingham | W | 0-2 |
| England EFL Trophy | 2018/09/04 18:45 | Portsmouth v Gillingham | L | 4-0 |
| England League 1 | 2018/03/10 15:00 | Portsmouth v Gillingham | W | 1-3 |
Home History
| Club Friendly List | 2021/07/31 13:00 | Leyton Orient v Gillingham | L | 2-0 |
| Club Friendly List | 2021/07/27 18:00 | Gillingham v Millwall | D | 1-1 |
| Club Friendly List | 2021/07/24 14:00 | Colchester v Gillingham | W | 0-2 |
| UK Friendlies | 2021/07/13 18:00 | Dartford v Gillingham | D | 0-0 |
| Club Friendly List | 2021/07/10 12:00 | Welling v Gillingham | D | 3-3 |
| England League 1 | 2021/05/09 11:00 | Gillingham v Plymouth | W | 1-0 |
| England League 1 | 2021/05/01 14:00 | Burton Albion v Gillingham | D | 1-1 |
| England League 1 | 2021/04/24 14:00 | Gillingham v Northampton | D | 2-2 |
Away History
| UK Friendlies | 2021/07/31 14:00 | Portsmouth v Peterborough | W | 2-0 |
| UK Friendlies | 2021/07/27 17:00 | Chelsea U23 v Portsmouth | L | 2-0 |
| Club Friendly List | 2021/07/24 14:00 | Luton v Portsmouth | D | 1-1 |
| Club Friendly List | 2021/07/20 13:00 | Bristol City v Portsmouth | D | 3-3 |
| Club Friendly List | 2021/07/10 14:00 | Havant and W v Portsmouth | W | 2-5 |
| England League 1 | 2021/05/09 11:00 | Portsmouth v Accrington Stanley | L | 0-1 |
| England League 1 | 2021/05/01 14:00 | AFC Wimbledon v Portsmouth | W | 1-3 |
| England League 1 | 2021/04/27 18:00 | Accrington Stanley v Portsmouth | D | 3-3 |