[7] Ayub/Singh 3-1 Milton Keynes Dons [18] 2019-12-31 23:45
Stadium: Fratton Park Round: 29
Referee: Kevin Johnson Home Manager: Kenneth Francis Jackett Away Manager: Russell Martin
Head to Head
| England League 1 | 2019/12/29 15:00 | Milton Keynes Dons v Portsmouth | L | 3-1 |
| England League 1 | 2018/02/10 15:00 | Milton Keynes Dons v Portsmouth | W | 1-2 |
| England League 1 | 2017/10/14 14:00 | Portsmouth v Milton Keynes Dons | W | 2-0 |
Home History
| England League 1 | 2019/12/29 15:00 | Milton Keynes Dons v Portsmouth | L | 3-1 |
| England League 1 | 2019/12/26 15:00 | Portsmouth v Wycombe | W | 2-0 |
| England League 1 | 2019/12/21 15:00 | Portsmouth v Ipswich | W | 1-0 |
| England League 1 | 2019/12/14 15:00 | Accrington Stanley v Portsmouth | L | 4-1 |
| England League 1 | 2019/12/07 15:00 | Portsmouth v Peterborough | D | 2-2 |
| England EFL Trophy | 2019/12/03 19:45 | Portsmouth v Northampton | W | 2-1 |
| England FA Cup | 2019/11/30 15:00 | Portsmouth v Altrincham | W | 2-1 |
| England League 1 | 2019/11/26 19:45 | Portsmouth v Rotherham | W | 3-2 |
Away History
| England League 1 | 2019/12/29 15:00 | Milton Keynes Dons v Portsmouth | W | 3-1 |
| England League 1 | 2019/12/26 15:00 | Southend v Milton Keynes Dons | D | 2-2 |
| England League 1 | 2019/12/21 13:00 | Gillingham v Milton Keynes Dons | L | 3-1 |
| England League 1 | 2019/12/14 15:00 | Milton Keynes Dons v Oxford Utd | W | 1-0 |
| England League 1 | 2019/12/07 15:00 | Doncaster v Milton Keynes Dons | D | 1-1 |
| England EFL Trophy | 2019/12/03 19:45 | Milton Keynes Dons v Coventry | W | 2-0 |
| England League 1 | 2019/11/23 15:00 | Milton Keynes Dons v Rotherham | L | 2-3 |
| England League 1 | 2019/11/16 15:00 | Bolton v Milton Keynes Dons | L | 1-0 |