| 1 | Tue 20 Oct | 266-2 v Hayes & Yeading UnitedHayes & Yeading United 2-6 Hampton & Richmond Borough | Middlesex Senior Cup Second Round |
| 2 | Sat 24 Oct | 26 3-4 v Truro CityHampton & Richmond Borough 3-4 Truro City | Enterprise National League South |
| 3 | Tue 27 Oct | 26 2-2 v Billericay TownBillericay Town 2-2 Hampton & Richmond Borough | Enterprise National League South |
| 4 | Sat 31 Oct | 260-1 v Braintree TownBraintree Town 1-0 Hampton & Richmond Borough | Enterprise National League South |
| 5 | Tue 3 Nov | 262-3 v Dorking WanderersDorking Wanderers 3-2 Hampton & Richmond Borough | Enterprise National League South |
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