Head to Head
| England Southern Premier League South | 2024/08/18 14:00 | Winchester City v Gosport Borough | W | 0-2 |
| England Southern Premier League South | 2024/04/01 14:00 | Gosport Borough v Winchester City | W | 2-1 |
| England Southern Premier League South | 2024/01/01 15:00 | Winchester City v Gosport Borough | D | 1-1 |
| England Southern Premier League South | 2023/01/02 15:00 | Gosport Borough v Winchester City | D | 2-2 |
| England Southern Premier League South | 2022/08/29 14:00 | Winchester City v Gosport Borough | W | 0-1 |
| Club Friendly List | 2015/07/04 14:00 | Winchester City v Gosport Borough | D | 0-0 |
Home History
| England Southern Premier League South | 2024/12/26 15:00 | Havant and W v Gosport Borough | L | 3-1 |
| England Southern Premier League South | 2024/12/21 15:00 | Gosport Borough v Hungerford Town | W | 1-0 |
| England Southern Premier League South | 2024/12/14 15:00 | Hanwell Town v Gosport Borough | D | 0-0 |
| England Southern Premier League South | 2024/11/30 14:00 | Gosport Borough v Plymouth Parkway | D | 0-0 |
| England Southern Premier League South | 2024/11/23 15:00 | Chertsey Town v Gosport Borough | W | 0-2 |
| England FA Trophy | 2024/11/16 15:00 | Gosport Borough v Tonbridge Angels | W | 1-0 |
| England Southern Premier League South | 2024/11/13 19:45 | Gosport Borough v Dorchester | D | 2-2 |
| England Southern Premier League South | 2024/11/02 15:00 | Poole Town v Gosport Borough | W | 1-3 |
Away History
| England Southern Premier League South | 2024/12/26 13:00 | Winchester City v AFC Totton | L | 1-4 |
| England Southern Premier League South | 2024/12/21 15:00 | Wimborne Town v Winchester City | W | 2-4 |
| England Southern Premier League South | 2024/12/17 19:45 | Winchester City v Basingstoke | L | 2-4 |
| England Southern Premier League South | 2024/12/14 15:00 | Winchester City v Bracknell Town | D | 0-0 |
| England Southern Premier League South | 2024/11/30 15:00 | Sholing v Winchester City | W | 0-1 |
| England Southern Premier League South | 2024/11/23 15:00 | Winchester City v Havant and W | L | 1-3 |
| England FA Trophy | 2024/11/16 15:00 | Winchester City v Sittingbourne | L | 5-6 |
| England Southern Premier League South | 2024/11/09 15:00 | Frome Town v Winchester City | W | 0-1 |