Head to Head
| England Southern Premier League South | 2023/09/09 14:00 | Didcot Town v Winchester City | L | 1-0 |
Home History
| England Southern Premier League South | 2024/01/20 15:00 | Walton & Hersham v Winchester City | L | 3-1 |
| England Southern Premier League South | 2024/01/13 15:00 | Sholing v Winchester City | L | 5-1 |
| England Southern Premier League South | 2024/01/01 15:00 | Winchester City v Gosport Borough | D | 1-1 |
| England Southern Premier League South | 2023/12/26 15:00 | Salisbury FC v Winchester City | D | 2-2 |
| England Southern Premier League South | 2023/12/23 15:00 | Winchester City v Hayes & Yeading | D | 1-1 |
| England Southern Premier League South | 2023/12/16 15:00 | AFC Totton v Winchester City | D | 1-1 |
| England Southern Premier League South | 2023/12/05 19:45 | Winchester City v Bracknell Town | W | 5-0 |
| England Southern Premier League South | 2023/11/28 19:45 | Winchester City v Walton & Hersham | W | 2-1 |
Away History
| England Southern Premier League South | 2024/01/13 15:00 | Didcot Town v Bracknell Town | W | 1-0 |
| England Southern Premier League South | 2024/01/06 15:00 | Didcot Town v Chesham | D | 1-1 |
| England Southern Premier League South | 2023/12/30 15:00 | Swindon Supermarine v Didcot Town | L | 4-1 |
| England Southern Premier League South | 2023/12/26 12:30 | Didcot Town v Hungerford Town | L | 0-1 |
| England Southern Premier League South | 2023/12/23 15:00 | Basingstoke v Didcot Town | W | 2-4 |
| England Southern Premier League South | 2023/12/16 15:00 | Didcot Town v Tiverton Town | D | 0-0 |
| England Southern Premier League South | 2023/12/12 19:45 | Hendon v Didcot Town | L | 3-1 |
| England Southern Premier League South | 2023/11/25 15:00 | Gosport Borough v Didcot Town | D | 0-0 |