| 1 | Sat 8 Aug | 12-1 v AFC Croydon AthleticAFC Croydon Athletic 1-2 Sittingbourne | Isthmian League - South East Division |
| 2 | Sat 15 Aug | 11-1 v Cray Valley PMSittingbourne 1-1 Cray Valley PM | Isthmian League - South East Division |
| 3 | Tue 18 Aug | 12-1 v Whitstable TownWhitstable Town 1-2 Sittingbourne | Isthmian League - South East Division |
| 4 | Sat 22 Aug | 12-1 v Erith & BelvedereErith & Belvedere 1-2 Sittingbourne | Emirates FA Cup Preliminary Round |
| 5 | Mon 31 Aug | 13-2 v Ashford UnitedSittingbourne 3-2 Ashford United | Isthmian League - South East Division |
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