| 1 | Sat 30 Aug | 1 3-3 v WorthingWorthing 3-3 Maidstone United | Enterprise National League South |
| 2 | Fri 12 Sep | 10-2 v Folkestone InvictaFolkestone Invicta 2-0 Maidstone United | Emirates FA Cup Second Qualifying Round |
| 3 | Sat 18 Oct | 12-0 v FarnboroughFarnborough 0-2 Maidstone United | Enterprise National League South |
| 4 | Sat 20 Dec | 10-0 v Hampton & Richmond BoroughHampton & Richmond Borough 0-0 Maidstone United | Enterprise National League South |
| 5 | Tue 30 Dec | 12-1 v HornchurchHornchurch 1-2 Maidstone United | Enterprise National League South |
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