| FA Trophy | Winchester City | Sittingbourne | 16‑Nov | 1-1 | |
| Non League Premier - Southern South | Frome Town | Winchester City | 09‑Nov | 0-1 | |
| Non League Premier - Southern South | Hanwell Town | Winchester City | 02‑Nov | 1-1 | |
| FA Trophy | Tavistock | Winchester City | 26‑Oct | 0-4 | |
| Non League Premier - Southern South | Winchester City | Gloucester City | 22‑Oct | 2-4 | |
| Non League Premier - Southern South | Winchester City | Walton & Hersham | 19‑Oct | 2-1 | |
| Non League Premier - Southern South | Swindon Supermarine | Winchester City | 15‑Oct | 2-0 | |
| Non League Premier - Southern South | Winchester City | Hungerford Town | 12‑Oct | 2-2 | |
| Non League Premier - Southern South | Winchester City | Poole Town | 08‑Oct | 1-1 | |
| FA Trophy | Winchester City | Swindon Supermarine | 05‑Oct | 5-2 | |
| FA Cup | Weymouth | Winchester City | 01‑Oct | 3-0 | |
| FA Cup | Winchester City | Weymouth | 28‑Sep | 2-2 | |
| Non League Premier - Southern South | Merthyr Town | Winchester City | 24‑Sep | 3-1 | |
| Non League Premier - Southern South | Tiverton Town | Winchester City | 21‑Sep | 2-1 | |
| FA Cup | Hungerford Town | Winchester City | 17‑Sep | 0-1 | |
| FA Cup | Winchester City | Hungerford Town | 14‑Sep | 1-1 | |
| Non League Premier - Southern South | Chertsey Town | Winchester City | 07‑Sep | 3-3 | |
| FA Cup | Tavistock | Winchester City | 31‑Aug | 0-1 | |
| Non League Premier - Southern South | Winchester City | Dorchester Town | 28‑Aug | 0-0 | |
| Non League Premier - Southern South | Plymouth Parkway | Winchester City | 24‑Aug | 0-3 | |
| Non League Premier - Southern South | Winchester City | Gosport Borough | 18‑Aug | 0-2 | |
| Non League Premier - Southern South | Winchester City | Wimborne Town | 14‑Aug | 2-4 | |
| Non League Premier - Southern South | Marlow | Winchester City | 10‑Aug | 1-1 | |
