| 1 | Mon 5 Aug | 52-1 v Leyton OrientCheshunt 2-1 Leyton Orient | Friendly |
| 2 | Sat 10 Aug | 123-2 v Bognor Regis TownCheshunt 3-2 Bognor Regis Town | Isthmian League - Premier Division |
| 3 | Tue 13 Aug | 121-1 v Bowers & PitseaBowers & Pitsea 1-1 Cheshunt | Isthmian League - Premier Division |
| 4 | Sat 17 Aug | 122-4 v Cray Valley PMCray Valley PM 4-2 Cheshunt | Isthmian League - Premier Division |
| 5 | Sat 24 Aug | 121-1 v Billericay TownCheshunt 1-1 Billericay Town | Isthmian League - Premier Division |
| 6 | Mon 26 Aug | 120-2 v HendonHendon 2-0 Cheshunt | Isthmian League - Premier Division |
| 7 | Sun 1 Sep | 132-1 v Great Yarmouth TownGreat Yarmouth Town 1-2 Cheshunt | Emirates FA Cup First Qualifying Round |
| 8 | Sat 7 Sep | 122-3 v Chichester CityCheshunt 2-3 Chichester City | Isthmian League - Premier Division |
| 9 | Sat 14 Sep | 12 0-1 v King's Lynn TownKing's Lynn Town 1-0 Cheshunt | Emirates FA Cup Second Qualifying Round |
| 10 | Sat 5 Oct | 12 0-3 v Dover AthleticDover Athletic 3-0 Cheshunt | Isuzu FA Trophy Third Qualifying Round |
| 11 | Tue 22 Oct | 141-1 v Potters Bar TownCheshunt 1-1 Potters Bar Town | Velocity Cup Third Round |
| 12 | Sat 26 Oct | 140-1 v Cray WanderersCheshunt 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 13 | Tue 29 Oct | 60-1 v Canvey IslandCheshunt 0-1 Canvey Island | Isthmian League - Premier Division |
| 14 | Sat 2 Nov | 15 4-0 v Bognor Regis TownBognor Regis Town 0-4 Cheshunt | Isthmian League - Premier Division |
| 15 | Sat 9 Nov | 61-2 v DartfordDartford 2-1 Cheshunt | Isthmian League - Premier Division |
| 16 | Tue 19 Nov | 60-3 v Billericay TownBillericay Town 3-0 Cheshunt | Velocity Cup Fourth Round |
| 17 | Sat 23 Nov | 61-1 v Carshalton AthleticCarshalton Athletic 1-1 Cheshunt | Isthmian League - Premier Division |
| 18 | Sat 30 Nov | 61-1 v Dulwich HamletCheshunt 1-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 19 | Tue 10 Dec | 60-1 v Chatham TownCheshunt 0-1 Chatham Town | Isthmian League - Premier Division |
| 20 | Sat 14 Dec | 61-3 v HorshamHorsham 3-1 Cheshunt | Isthmian League - Premier Division |
| 21 | Tue 17 Dec | 61-0 v Bowers & PitseaCheshunt 1-0 Bowers & Pitsea | Isthmian League - Premier Division |
| 22 | Sat 21 Dec | 61-2 v Dover AthleticCheshunt 1-2 Dover Athletic | Isthmian League - Premier Division |
| 23 | Thu 26 Dec | 61-0 v Wingate & FinchleyWingate & Finchley 0-1 Cheshunt | Isthmian League - Premier Division |
| 24 | Sat 28 Dec | 64-4 v Cray Valley PMCheshunt 4-4 Cray Valley PM | Isthmian League - Premier Division |
| 25 | Sat 4 Jan | 6 2-2 v LewesLewes 2-2 Cheshunt | Isthmian League - Premier Division |
| 26 | Tue 7 Jan | 64-0 v Folkestone InvictaFolkestone Invicta 0-4 Cheshunt | Isthmian League - Premier Division |
| 27 | Tue 14 Jan | 127-4 v WareCheshunt 7-4 Ware | Hertfordshire County Cup Quarter Final |
| 28 | Sat 18 Jan | 6 1-4 v WhitehawkCheshunt 1-4 Whitehawk | Isthmian League - Premier Division |
| 29 | Sat 25 Jan | 62-1 v Potters Bar TownPotters Bar Town 1-2 Cheshunt | Isthmian League - Premier Division |
| 30 | Tue 28 Jan | 61-0 v Canvey IslandCanvey Island 0-1 Cheshunt | Isthmian League - Premier Division |
| 31 | Sat 1 Feb | 60-1 v Hashtag UnitedHashtag United 1-0 Cheshunt | Isthmian League - Premier Division |
| 32 | Tue 4 Feb | 62-2 v HendonCheshunt 2-2 Hendon | Isthmian League - Premier Division |
| 33 | Sat 8 Feb | 62-1 v Hastings UnitedCheshunt 2-1 Hastings United | Isthmian League - Premier Division |
| 34 | Sat 15 Feb | 61-2 v Cray WanderersCray Wanderers 2-1 Cheshunt | Isthmian League - Premier Division |
| 35 | Sat 22 Feb | 63-0 v DartfordCheshunt 3-0 Dartford | Isthmian League - Premier Division |
| 36 | Sat 1 Mar | 61-4 v Chatham TownChatham Town 4-1 Cheshunt | Isthmian League - Premier Division |
| 37 | Sat 8 Mar | 6 0-1 v Carshalton AthleticCheshunt 0-1 Carshalton Athletic | Isthmian League - Premier Division |
| 38 | Sat 15 Mar | 61-0 v Dulwich HamletDulwich Hamlet 0-1 Cheshunt | Isthmian League - Premier Division |
| 39 | Tue 18 Mar | 61-2 v Potters Bar TownCheshunt 1-2 Potters Bar Town | Hertfordshire County Cup Semi Final |
| 40 | Sat 22 Mar | 61-0 v Folkestone InvictaCheshunt 1-0 Folkestone Invicta | Isthmian League - Premier Division |
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