| Non League Premier - Isthmian | Cray Wanderers | Whitehawk | 12‑Dec | 1-2 | |
| Non League Premier - Isthmian | Potters Bar Town | Cray Wanderers | 06‑Dec | 0-2 | |
| Non League Premier - Isthmian | Canvey Island | Cray Wanderers | 29‑Nov | 1-1 | |
| Non League Premier - Isthmian | Cray Wanderers | Burgess Hill Town | 22‑Nov | 3-3 | |
| Non League Premier - Isthmian | Welling United | Cray Wanderers | 15‑Nov | 0-2 | |
| Non League Premier - Isthmian | Folkestone Invicta | Cray Wanderers | 11‑Nov | 8-1 | |
| Non League Premier - Isthmian | Cray Wanderers | Chichester City | 08‑Nov | 0-0 | |
| Non League Premier - Isthmian | Cheshunt | Cray Wanderers | 01‑Nov | 1-1 | |
| Non League Premier - Isthmian | Cray Wanderers | Dartford | 25‑Oct | 0-2 | |
| Non League Premier - Isthmian | Cray Wanderers | St Albans City | 21‑Oct | 1-1 | |
| Non League Premier - Isthmian | Chatham Town | Cray Wanderers | 18‑Oct | 3-3 | |
| Non League Premier - Isthmian | Dulwich Hamlet | Cray Wanderers | 11‑Oct | 1-1 | |
| FA Trophy | Bishop's Stortford | Cray Wanderers | 04‑Oct | 4-0 | |
| Non League Premier - Isthmian | Cray Wanderers | Dulwich Hamlet | 30‑Sep | 4-2 | |
| Non League Premier - Isthmian | Ramsgate | Cray Wanderers | 27‑Sep | 1-1 | |
| Non League Premier - Isthmian | Cray Wanderers | Hashtag United | 20‑Sep | 4-3 | |
| Non League Premier - Isthmian | Carshalton Athletic | Cray Wanderers | 13‑Sep | 2-2 | |
| Non League Premier - Isthmian | Lewes | Cray Wanderers | 06‑Sep | 2-2 | |
| FA Cup | Hanwell Town | Cray Wanderers | 02‑Sep | 1-0 | |
| FA Cup | Cray Wanderers | Hanwell Town | 30‑Aug | 2-2 | |
| Non League Premier - Isthmian | Cray Wanderers | Brentwood Town | 25‑Aug | 1-5 | |
| Non League Premier - Isthmian | Billericay Town | Cray Wanderers | 23‑Aug | 0-1 | |
| Non League Premier - Isthmian | Cray Wanderers | Wingate & Finchley | 16‑Aug | 3-2 | |
| Non League Premier - Isthmian | Cray Wanderers | Folkestone Invicta | 12‑Aug | 1-1 | |
| Non League Premier - Isthmian | Cray Wanderers | Canvey Island | 09‑Aug | 2-0 | |
| Friendlies Clubs | Cray Wanderers | Maidstone Utd | 02‑Aug | 2-0 | |
| Friendlies Clubs | Cray Wanderers | Ashford United | 26‑Jul | 3-2 | |
| Friendlies Clubs | Cray Wanderers | Sittingbourne | 22‑Jul | 3-1 | |
| Friendlies Clubs | Cray Wanderers | Bromley | 19‑Jul | 2-2 | |
