Head to Head
| England Southern Premier League South | 2023/01/28 15:00 | Bracknell Town v Winchester City | W | 3-1 |
| England Southern Premier League South | 2022/11/01 19:45 | Winchester City v Bracknell Town | W | 2-3 |
Home History
| England FA Trophy | 2023/11/18 15:00 | Bracknell Town v Horsham | L | 0-3 |
| England Southern Premier League South | 2023/11/14 19:45 | Dorchester v Bracknell Town | W | 1-2 |
| England Southern Premier League South | 2023/11/11 15:00 | Bracknell Town v Chesham | W | 4-0 |
| England FA Trophy | 2023/11/07 19:45 | Bracknell Town v Poole Town | D | 2-2 |
| England FA Cup | 2023/11/04 15:00 | Cambridge Utd v Bracknell Town | L | 2-1 |
| England Southern Premier League South | 2023/10/24 18:45 | Harrow Borough v Bracknell Town | W | 1-4 |
| England Southern Premier League South | 2023/10/21 14:00 | Bracknell Town v AFC Totton | L | 1-5 |
| England Southern Premier League South | 2023/10/17 18:45 | Bracknell Town v Basingstoke | W | 4-0 |
Away History
| England Southern Premier League South | 2023/11/14 19:45 | Hungerford Town v Winchester City | D | 2-2 |
| England Southern Premier League South | 2023/11/11 15:00 | Beaconsfield v Winchester City | W | 1-2 |
| England Southern Premier League South | 2023/10/24 18:45 | Merthyr Town v Winchester City | W | 1-2 |
| England Southern Premier League South | 2023/10/21 14:00 | Winchester City v Harrow Borough | L | 1-2 |
| England Southern Premier League South | 2023/10/14 14:00 | Hanwell Town v Winchester City | D | 4-4 |
| England FA Trophy | 2023/10/07 14:00 | Winchester City v Hungerford Town | L | 3-5 |
| England Southern Premier League South | 2023/10/03 18:45 | Winchester City v Plymouth Parkway | D | 1-1 |
| England FA Cup Qualification | 2023/09/30 14:00 | Winchester City v Maidstone Utd | L | 0-2 |