Stadium: Portman Road Stadium Round: 31
Referee: Steve Martin Home Manager: Kieran McKenna Away Manager: Stephen John Lovell
| England League 1 | 2021/03/06 13:00 | Gillingham v Ipswich | L | 3-1 |
| England League 1 | 2020/10/27 19:00 | Ipswich v Gillingham | W | 1-0 |
| England EFL Trophy | 2020/10/06 18:00 | Ipswich v Gillingham | W | 2-0 |
| England League 1 | 2019/12/26 15:00 | Ipswich v Gillingham | D | 0-0 |
| England EFL Trophy | 2019/10/08 18:45 | Ipswich v Gillingham | W | 4-0 |
| England League 1 | 2019/09/21 14:00 | Gillingham v Ipswich | W | 0-1 |
| Club Friendly List | 2017/07/22 14:00 | Gillingham v Ipswich | L | 2-1 |
| Club Friendly List | 2014/07/26 14:00 | Gillingham v Ipswich | W | 0-2 |
| England League 1 | 2021/09/18 14:00 | Lincoln City v Ipswich | W | 0-1 |
| England EFL Trophy | 2021/09/14 18:45 | Ipswich v West Ham U21 | L | 1-2 |
| England League 1 | 2021/09/11 14:00 | Ipswich v Bolton | L | 2-5 |
| England League 1 | 2021/08/28 14:00 | Ipswich v AFC Wimbledon | D | 2-2 |
| England League 1 | 2021/08/21 14:00 | Ipswich v Milton Keynes Dons | D | 2-2 |
| England League 1 | 2021/08/17 18:45 | Cheltenham v Ipswich | L | 2-1 |
| England League 1 | 2021/08/14 14:00 | Burton Albion v Ipswich | L | 2-1 |
| England EFL Cup | 2021/08/10 18:45 | Ipswich v Newport County | L | 0-1 |
| England League 1 | 2021/09/21 18:45 | Gillingham v Charlton | D | 1-1 |
| England League 1 | 2021/09/18 14:00 | Gillingham v Milton Keynes Dons | L | 1-4 |
| England League 1 | 2021/09/11 14:00 | Burton Albion v Gillingham | D | 1-1 |
| England EFL Trophy | 2021/09/07 18:30 | Colchester v Gillingham | W | 0-1 |
| England League 1 | 2021/08/28 14:00 | Shrewsbury v Gillingham | L | 2-1 |
| England EFL Cup | 2021/08/24 18:45 | Gillingham v Cheltenham | L | 5-6 |
| England League 1 | 2021/08/21 14:00 | Gillingham v Morecambe | W | 2-1 |
| England League 1 | 2021/08/17 18:45 | AFC Wimbledon v Gillingham | D | 1-1 |