[1] Iska/Raman 2-0 Bolton [2] 2023-10-25 08:00
Stadium: Fratton Park Round: 21
Referee: Paul Howard Home Manager: John Mousinho Away Manager: Ian Ross Evatt
Head to Head
| England League 1 | 2023/02/28 19:45 | Portsmouth v Bolton | W | 3-1 |
| England League 1 | 2023/01/14 15:00 | Bolton v Portsmouth | L | 3-0 |
| England EFL Trophy | 2023/01/10 19:45 | Bolton v Portsmouth | L | 1-0 |
| England League 1 | 2022/04/05 19:00 | Bolton v Portsmouth | D | 1-1 |
| England League 1 | 2021/10/30 14:00 | Portsmouth v Bolton | W | 1-0 |
| England League 1 | 2020/01/18 15:00 | Bolton v Portsmouth | W | 0-1 |
| England League 1 | 2019/09/28 14:00 | Portsmouth v Bolton | W | 1-0 |
Home History
| England League 1 | 2023/10/24 18:45 | Cambridge Utd v Portsmouth | D | 0-0 |
| England League 1 | 2023/10/21 14:00 | Portsmouth v Carlisle | W | 1-0 |
| England EFL Trophy | 2023/10/10 18:45 | Portsmouth v Gillingham | W | 5-1 |
| England League 1 | 2023/10/07 14:00 | Portsmouth v Port Vale | W | 2-0 |
| England League 1 | 2023/10/03 18:45 | Portsmouth v Wycombe | W | 2-1 |
| England League 1 | 2023/09/30 14:00 | Wigan v Portsmouth | W | 1-2 |
| England League 1 | 2023/09/23 14:00 | Portsmouth v Lincoln City | W | 2-1 |
| England League 1 | 2023/09/19 18:45 | Barnsley v Portsmouth | W | 2-3 |
Away History
| England League 1 | 2023/10/24 18:45 | Wycombe v Bolton | W | 2-4 |
| England League 1 | 2023/10/21 14:00 | Bolton v Northampton | W | 2-1 |
| England League 1 | 2023/10/07 14:00 | Bolton v Carlisle | L | 1-3 |
| England League 1 | 2023/10/03 18:45 | Bolton v Stevenage | W | 3-2 |
| England League 1 | 2023/09/30 14:00 | Port Vale v Bolton | W | 0-1 |
| England EFL Trophy | 2023/09/26 18:45 | Bolton v Man Utd U21 | W | 8-1 |
| England League 1 | 2023/09/23 14:00 | Bolton v Peterborough | D | 1-1 |
| England League 1 | 2023/09/16 14:00 | Reading v Bolton | L | 2-1 |