Home History
| England FA Trophy | 2016/11/12 15:00 | Phoenix Sports v Winchester City | W | 1-3 |
| England Southern League Division One | 2016/10/26 18:45 | Winchester City v Bishops Cleeve | L | 1-2 |
| England FA Cup Qualification | 2016/10/01 14:00 | Harrow Borough v Winchester City | L | 2-1 |
| England FA Cup | 2016/09/17 14:00 | Winchester City v Truro City | W | 4-0 |
| England FA Cup | 2016/09/03 14:00 | Winchester City v Street | W | 4-2 |
| England FA Cup Qualification | 2015/09/29 18:45 | Maidenhead Utd v Winchester City | L | 4-2 |
| England FA Cup Qualification | 2015/09/26 14:00 | Winchester City v Maidenhead Utd | D | 1-1 |
| England FA Cup Qualification | 2015/09/12 14:00 | Swindon Supermarine v Winchester City | W | 0-4 |
Away History
| England Isthmian Premier Division | 2016/11/22 19:45 | Harrow Borough v Dulwich | W | 0-2 |
| England Isthmian Premier Division | 2016/11/19 15:00 | Dulwich v Worthing | W | 4-1 |
| England FA Trophy | 2016/11/12 15:00 | Dulwich v Chesham | W | 4-0 |
| England Isthmian Premier Division | 2016/11/05 15:00 | Needham Market v Dulwich | D | 1-1 |
| England Isthmian Premier Division | 2016/11/01 19:45 | Staines Town v Dulwich | L | 2-0 |
| England Isthmian Premier Division | 2016/10/22 14:00 | Dulwich v AFC Sudbury | W | 2-0 |
| England Isthmian Premier Division | 2016/10/18 18:45 | Dulwich v Harlow | W | 3-1 |
| England Isthmian Premier Division | 2016/10/15 14:00 | Leatherhead v Dulwich | D | 2-2 |