| 1 | Sat 9 Aug | 2 4-2 v Welling UnitedCheshunt 4-2 Welling United | Isthmian League - Premier Division |
| 2 | Tue 12 Aug | 2 4-1 v Canvey IslandCanvey Island 1-4 Cheshunt | Isthmian League - Premier Division |
| 3 | Sat 16 Aug | 20-1 v Chatham TownChatham Town 1-0 Cheshunt | Isthmian League - Premier Division |
| 4 | Sat 23 Aug | 23-1 v Hashtag UnitedCheshunt 3-1 Hashtag United | Isthmian League - Premier Division |
| 5 | Mon 25 Aug | 2 2-1 v St Albans CitySt Albans City 1-2 Cheshunt | Isthmian League - Premier Division |
| 6 | Sat 30 Aug | 21-2 v LeistonCheshunt 1-2 Leiston | Emirates FA Cup First Qualifying Round |
| 7 | Sat 6 Sep | 21-1 v Burgess Hill TownCheshunt 1-1 Burgess Hill Town | Isthmian League - Premier Division |
| 8 | Tue 9 Sep | 22-2 v Billericay TownCheshunt 2-2 Billericay Town | Isthmian League - Premier Division |
| 9 | Sat 4 Oct | 22-1 v Carshalton AthleticCarshalton Athletic 1-2 Cheshunt | Isuzu FA Trophy Third Qualifying Round |
| 10 | Sat 11 Oct | 21-1 v Cray Valley PMCheshunt 1-1 Cray Valley PM | Isthmian League - Premier Division |
| 11 | Tue 14 Oct | 2 1-1 v Billericay TownBillericay Town 1-1 Cheshunt | Isthmian League - Premier Division |
| 12 | Sat 18 Oct | 22-3 v Wingate & FinchleyCheshunt 2-3 Wingate & Finchley | Isthmian League - Premier Division |
| 13 | Tue 21 Oct | 24-0 v Harrow BoroughHarrow Borough 0-4 Cheshunt | London Senior Cup |
| 14 | Sat 25 Oct | 21-0 v Wingate & FinchleyWingate & Finchley 0-1 Cheshunt | Isuzu FA Trophy First Round |
| 15 | Tue 28 Oct | 21-2 v LewesLewes 2-1 Cheshunt | Isthmian League - Premier Division |
| 16 | Sat 1 Nov | 21-1 v Cray WanderersCheshunt 1-1 Cray Wanderers | Isthmian League - Premier Division |
| 17 | Tue 4 Nov | 23-0 v BarkingBarking 0-3 Cheshunt | London Senior Cup |
| 18 | Sat 8 Nov | 21-1 v RamsgateRamsgate 1-1 Cheshunt | Isthmian League - Premier Division |
| 19 | Sat 15 Nov | 21-1 v Bishop's StortfordBishop's Stortford 1-1 Cheshunt | Isuzu FA Trophy Second Round |
| 20 | Tue 18 Nov | 25-1 v St Albans CitySt Albans City 1-5 Cheshunt | Velocity Cup Third Round |
| 21 | Sat 22 Nov | 22-4 v Folkestone InvictaCheshunt 2-4 Folkestone Invicta | Isthmian League - Premier Division |
| 22 | Tue 25 Nov | 2 2-0 v Canvey IslandCheshunt 2-0 Canvey Island | Isthmian League - Premier Division |
| 23 | Sat 29 Nov | 21-3 v Welling UnitedWelling United 3-1 Cheshunt | Isthmian League - Premier Division |
| 24 | Tue 9 Dec | 22-2 v Brentwood TownBrentwood Town 2-2 Cheshunt | Isthmian League - Premier Division |
| 25 | Sat 13 Dec | 21-2 v WealdstoneWealdstone 2-1 Cheshunt | Isuzu FA Trophy Third Round |
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