Head to Head
| England Southern Premier League South | 2022/08/13 14:00 | Harrow Borough v Winchester City | D | 1-1 |
| England FA Cup Qualification | 2016/10/01 14:00 | Harrow Borough v Winchester City | L | 2-1 |
Home History
| England Southern Premier League South | 2023/02/04 15:00 | Winchester City v Merthyr Town | D | 2-2 |
| England Southern Premier League South | 2023/01/28 15:00 | Bracknell Town v Winchester City | L | 3-1 |
| England Southern Premier League South | 2023/01/14 15:00 | Dorchester v Winchester City | L | 2-1 |
| England Southern Premier League South | 2023/01/07 15:00 | Met Police v Winchester City | L | 2-1 |
| England Southern Premier League South | 2023/01/02 15:00 | Gosport Borough v Winchester City | D | 2-2 |
| England Southern Premier League South | 2022/12/26 15:00 | Winchester City v Salisbury FC | L | 0-1 |
| England Southern Premier League South | 2022/12/03 15:00 | Hayes & Yeading v Winchester City | L | 4-0 |
| England Southern Premier League South | 2022/11/26 15:00 | Winchester City v Dorchester | D | 1-1 |
Away History
| England Southern Premier League South | 2023/02/04 15:00 | Harrow Borough v Beaconsfield | W | 1-0 |
| England FA Trophy | 2023/01/31 19:45 | Harrow Borough v Halifax | L | 7-8 |
| England Southern Premier League South | 2023/01/28 15:00 | Hendon v Harrow Borough | L | 3-0 |
| England Southern Premier League South | 2023/01/07 15:00 | Harrow Borough v Weston Super Mare | L | 1-5 |
| England Southern Premier League South | 2023/01/02 15:00 | Hayes & Yeading v Harrow Borough | D | 2-2 |
| England Southern Premier League South | 2022/12/26 15:00 | Harrow Borough v Met Police | L | 0-2 |
| England FA Trophy | 2022/12/21 19:45 | Swindon Supermarine v Harrow Borough | W | 1-2 |
| England Southern Premier League South | 2022/12/07 19:45 | Harrow Borough v Hartley Wintney | W | 1-0 |