| 1 | Tue 22 Sep | 11-5 v Brentwood TownBrentwood Town 5-1 Maldon & Tiptree | Isthmian League - Premier Division |
| 2 | Tue 29 Sep | 11-5 v Cray WanderersMaldon & Tiptree 1-5 Cray Wanderers | Isthmian League - Premier Division |
| 3 | Sat 3 Oct | 11-4 v Burgess Hill TownBurgess Hill Town 4-1 Maldon & Tiptree | Isthmian League - Premier Division |
| 4 | Tue 6 Oct | 10-1 v Welling UnitedMaldon & Tiptree 0-1 Welling United | Isthmian League - Premier Division |
| 5 | Sat 10 Oct | 11-2 v AFC WhyteleafeMaldon & Tiptree 1-2 AFC Whyteleafe | Isthmian League - Premier Division |
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