| 1 | Tue 24 Oct 2023 | 21-2 v Canvey IslandCanvey Island 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 2 | Sat 4 Nov 2023 | 23-1 v Wingate & FinchleyWingate & Finchley 1-3 Cray Wanderers | Isthmian League - Premier Division |
| 3 | Wed 8 Nov 2023 | 24-2 v Tooting & Mitcham UnitedCray Wanderers 4-2 Tooting & Mitcham United | London County Cup First Round |
| 4 | Sat 11 Nov 2023 | 2 1-0 v Carshalton AthleticCray Wanderers 1-0 Carshalton Athletic | Isthmian League - Premier Division |
| 5 | Sat 25 Nov 2023 | 21-1 v Dulwich HamletCray Wanderers 1-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 6 | Wed 29 Nov 2023 | 22-2 v WhitehawkCray Wanderers 2-2 Whitehawk | Isthmian League - Premier Division |
| 7 | Sun 10 Dec 2023 | 2 3-3 v Haringey BoroughCray Wanderers 3-3 Haringey Borough | Isthmian League - Premier Division |
| 8 | Sat 16 Dec 2023 | 20-1 v Hashtag UnitedHashtag United 1-0 Cray Wanderers | Isthmian League - Premier Division |
| 9 | Fri 29 Dec 2023 | 22-0 v Enfield TownCray Wanderers 2-0 Enfield Town | Isthmian League - Premier Division |
| 10 | Mon 1 Jan 2024 | 20-0 v Hastings UnitedCray Wanderers 0-0 Hastings United | Isthmian League - Premier Division |
| 11 | Tue 9 Jan 2024 | 21-2 v Bognor Regis TownBognor Regis Town 2-1 Cray Wanderers | Isthmian League - Premier Division |
| 12 | Wed 24 Jan 2024 | 23-0 v FisherCray Wanderers 3-0 Fisher | London County Cup Second Round |
| 13 | Sat 27 Jan 2024 | 2 1-0 v Wingate & FinchleyCray Wanderers 1-0 Wingate & Finchley | Isthmian League - Premier Division |
| 14 | Sat 3 Feb 2024 | 22-1 v Carshalton AthleticCarshalton Athletic 1-2 Cray Wanderers | Isthmian League - Premier Division |
| 15 | Tue 6 Feb 2024 | 2 2-2 v Folkestone InvictaFolkestone Invicta 2-2 Cray Wanderers | Isthmian League - Premier Division |
| 16 | Sun 11 Feb 2024 | 21-1 v Concord RangersCray Wanderers 1-1 Concord Rangers | Isthmian League - Premier Division |
| 17 | Sat 17 Feb 2024 | 21-0 v CheshuntCheshunt 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 18 | Wed 21 Feb 2024 | 22-1 v Canvey IslandCray Wanderers 2-1 Canvey Island | Isthmian League - Premier Division |
| 19 | Wed 13 Mar 2024 | 21-2 v Potters Bar TownCray Wanderers 1-2 Potters Bar Town | Isthmian League - Premier Division |
| 20 | Fri 29 Mar 2024 | 22-2 v Chatham TownCray Wanderers 2-2 Chatham Town | Isthmian League - Premier Division |
| 21 | Fri 5 Apr 2024 | 2 1-3 v Hashtag UnitedCray Wanderers 1-3 Hashtag United | Isthmian League - Premier Division |
| 22 | Tue 9 Apr 2024 | 20-2 v HornchurchHornchurch 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 23 | Sat 13 Apr 2024 | 20-2 v HorshamHorsham 2-0 Cray Wanderers | Isthmian League - Premier Division |
| 24 | Tue 16 Apr 2024 | 21-2 v DartfordCray Wanderers 1-2 Dartford | London County Cup Quarter Final |
| 25 | Sat 20 Apr 2024 | 21-5 v Bognor Regis TownCray Wanderers 1-5 Bognor Regis Town | Isthmian League - Premier Division |
| 26 | Sat 27 Apr 2024 | 26-2 v Dulwich HamletDulwich Hamlet 2-6 Cray Wanderers | Isthmian League - Premier Division |
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