Saturday 5 September
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |   Lewes vs Cray Wanderers | 2 - 2 | FA Cup Stage : 1st Round Qualifying | - |
Tuesday 8 September
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 19h45 | Cray Wanderers vs Lewes | 1 - 0 | FA Cup Stage : 1st Round Qualifying Replays | - |
Saturday 19 September
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Cray Wanderers vs Maidstone Utd | 1 - 1 | FA Cup Stage : 2nd Round Qualifying | - |
Tuesday 22 September
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 19h45 | Maidstone Utd vs Cray Wanderers | 0 - 2 | FA Cup Stage : 2nd Round Qualifying Replays | - |
Saturday 3 October
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Cray Wanderers vs Chippenham Town | 3 - 0 | FA Cup Stage : 3rd Round Qualifying | - |
Saturday 17 October
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h00 |  Bedford Town vs Cray Wanderers | 0 - 0 | FA Cup Stage : 4th Round Qualifying | The New Eyrie |
Tuesday 20 October
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 19h45 | Cray Wanderers vs Bedford Town | 2 - 2 | FA Cup Stage : 4th Round Qualifying | Flamingo Park |
Sunday 8 November
| Time | Match | Score | Competition | Stadium |
|---|---|---|---|---|
| 15h15 |  Cray Wanderers vs Stockport County | - | FA Cup Stage : 1/128-finals | - |
