| 1 | Sat 26 Aug 2023 | 22-0 v Potters Bar TownChatham Town 2-0 Potters Bar Town |
| 2 | Mon 28 Aug 2023 | 2 5-2 v Dulwich HamletDulwich Hamlet 2-5 Chatham Town |
| 3 | Sat 9 Sep 2023 | 21-5 v Cray WanderersChatham Town 1-5 Cray Wanderers |
| 4 | Sat 16 Sep 2023 | 2 0-0 v Potters Bar TownPotters Bar Town 0-0 Chatham Town |
| 5 | Sat 23 Sep 2023 | 23-0 v LewesChatham Town 3-0 Lewes |
| 6 | Sat 14 Oct 2023 | 22-2 v Carshalton AthleticChatham Town 2-2 Carshalton Athletic |
| 7 | Tue 17 Oct 2023 | 20-2 v MargateMargate 2-0 Chatham Town |
| 8 | Sat 21 Oct 2023 | 23-1 v Concord RangersConcord Rangers 1-3 Chatham Town |
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