| 1 | Sat 4 Oct | 11-3 v Herne BayCrowborough Athletic 1-3 Herne Bay | Isthmian League - South East Division |
| 2 | Tue 14 Oct | 10-2 v AFC Croydon AthleticCrowborough Athletic 0-2 AFC Croydon Athletic | Isthmian League - South East Division |
| 3 | Tue 21 Oct | 11-5 v Deal TownDeal Town 5-1 Crowborough Athletic | Isthmian League - South East Division |
| 4 | Tue 28 Oct | 14-0 v SittingbourneCrowborough Athletic 4-0 Sittingbourne | Velocity Cup Second Round |
| 5 | Tue 4 Nov | 11-1 v Sheppey UnitedSheppey United 1-1 Crowborough Athletic | Velocity Cup Third Round |
| 6 | Tue 11 Nov | 11-1 v HassocksHassocks 1-1 Crowborough Athletic | Isthmian League - South East Division |
| 7 | Tue 18 Nov | 11-2 v SittingbourneCrowborough Athletic 1-2 Sittingbourne | Isthmian League - South East Division |
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