Head to Head
| 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 | 2024/03/29 15:00 | Basingstoke v Gosport Borough | L | 3-0 |
| England Southern Premier League South | 2024/03/23 15:00 | Didcot Town v Gosport Borough | W | 0-4 |
| England Southern Premier League South | 2024/03/16 15:00 | Gosport Borough v Harrow Borough | W | 1-0 |
| England Southern Premier League South | 2024/03/09 15:00 | Hayes & Yeading v Gosport Borough | W | 0-3 |
| England Southern Premier League South | 2024/03/06 19:45 | Gosport Borough v Poole Town | L | 1-2 |
| England Southern Premier League South | 2024/03/02 15:00 | Gosport Borough v Beaconsfield | L | 1-2 |
| England Southern Premier League South | 2024/02/20 19:45 | Hungerford Town v Gosport Borough | W | 0-2 |
| England Southern Premier League South | 2024/02/17 15:00 | Gosport Borough v Salisbury FC | D | 1-1 |
Away History
| England Southern Premier League South | 2024/03/30 15:00 | Winchester City v Dorchester | D | 1-1 |
| England Southern Premier League South | 2024/03/23 15:00 | Hendon v Winchester City | L | 2-1 |
| England Southern Premier League South | 2024/03/21 19:45 | Plymouth Parkway v Winchester City | D | 1-1 |
| England Southern Premier League South | 2024/03/16 15:00 | Winchester City v Poole Town | W | 4-0 |
| England Southern Premier League South | 2024/02/24 15:00 | Harrow Borough v Winchester City | W | 1-2 |
| England Southern Premier League South | 2024/02/17 15:00 | Winchester City v Hanwell Town | D | 1-1 |
| England Southern Premier League South | 2024/02/06 19:45 | Winchester City v Swindon Supermarine | D | 2-2 |
| England Southern Premier League South | 2024/02/03 15:00 | Winchester City v Chesham | L | 0-3 |