| 1 | Sat 10 Aug | 83-2 v Bognor Regis TownCheshunt 3-2 Bognor Regis Town | Isthmian League - Premier Division |
| 2 | Tue 13 Aug | 81-1 v Bowers & PitseaBowers & Pitsea 1-1 Cheshunt | Isthmian League - Premier Division |
| 3 | Sat 17 Aug | 82-4 v Cray Valley PMCray Valley PM 4-2 Cheshunt | Isthmian League - Premier Division |
| 4 | Sat 24 Aug | 8 1-1 v Billericay TownCheshunt 1-1 Billericay Town | Isthmian League - Premier Division |
| 5 | Mon 26 Aug | 80-2 v HendonHendon 2-0 Cheshunt | Isthmian League - Premier Division |
| 6 | Sat 7 Sep | 82-3 v Chichester CityCheshunt 2-3 Chichester City | Isthmian League - Premier Division |
| 7 | Sat 14 Sep | 8 0-1 v King's Lynn TownKing's Lynn Town 1-0 Cheshunt | Emirates FA Cup Second Qualifying Round |
| 8 | Sat 21 Sep | 83-4 v Hashtag UnitedCheshunt 3-4 Hashtag United | Isthmian League - Premier Division |
| 9 | Sat 5 Oct | 80-3 v Dover AthleticDover Athletic 3-0 Cheshunt | Isuzu FA Trophy Third Qualifying Round |
| 10 | Sat 12 Oct | 80-1 v Potters Bar TownCheshunt 0-1 Potters Bar Town | Isthmian League - Premier Division |
| 11 | Tue 15 Oct | 83-2 v Hastings UnitedHastings United 2-3 Cheshunt | Isthmian League - Premier Division |
| 12 | Sat 19 Oct | 8 2-0 v WhitehawkWhitehawk 0-2 Cheshunt | Isthmian League - Premier Division |
| 13 | Tue 22 Oct | 8 1-1 v Potters Bar TownCheshunt 1-1 Potters Bar Town | Velocity Cup Third Round |
| 14 | Sat 26 Oct | 80-1 v Cray WanderersCheshunt 0-1 Cray Wanderers | Isthmian League - Premier Division |
| 15 | Tue 29 Oct | 80-1 v Canvey IslandCheshunt 0-1 Canvey Island | Isthmian League - Premier Division |
| 16 | Sat 2 Nov | 84-0 v Bognor Regis TownBognor Regis Town 0-4 Cheshunt | Isthmian League - Premier Division |
| 17 | Sat 9 Nov | 81-2 v DartfordDartford 2-1 Cheshunt | Isthmian League - Premier Division |
| 18 | Tue 19 Nov | 80-3 v Billericay TownBillericay Town 3-0 Cheshunt | Velocity Cup Fourth Round |
| 19 | Sat 23 Nov | 81-1 v Carshalton AthleticCarshalton Athletic 1-1 Cheshunt | Isthmian League - Premier Division |
| 20 | Sat 30 Nov | 81-1 v Dulwich HamletCheshunt 1-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 21 | Tue 10 Dec | 80-1 v Chatham TownCheshunt 0-1 Chatham Town | Isthmian League - Premier Division |
| 22 | Sat 14 Dec | 81-3 v HorshamHorsham 3-1 Cheshunt | Isthmian League - Premier Division |
| 23 | Tue 17 Dec | 51-0 v Bowers & PitseaCheshunt 1-0 Bowers & Pitsea | Isthmian League - Premier Division |
| 24 | Sat 21 Dec | 41-2 v Dover AthleticCheshunt 1-2 Dover Athletic | Isthmian League - Premier Division |
| 25 | Thu 26 Dec | 41-0 v Wingate & FinchleyWingate & Finchley 0-1 Cheshunt | Isthmian League - Premier Division |
| 26 | Sat 28 Dec | 44-4 v Cray Valley PMCheshunt 4-4 Cray Valley PM | Isthmian League - Premier Division |
| 27 | Sat 4 Jan | 42-2 v LewesLewes 2-2 Cheshunt | Isthmian League - Premier Division |
| 28 | Tue 7 Jan | 44-0 v Folkestone InvictaFolkestone Invicta 0-4 Cheshunt | Isthmian League - Premier Division |
| 29 | Tue 14 Jan | 47-4 v WareCheshunt 7-4 Ware | Hertfordshire County Cup Quarter Final |
| 30 | Sat 18 Jan | 41-4 v WhitehawkCheshunt 1-4 Whitehawk | Isthmian League - Premier Division |
| 31 | Sat 25 Jan | 82-1 v Potters Bar TownPotters Bar Town 1-2 Cheshunt | Isthmian League - Premier Division |
| 32 | Tue 28 Jan | 41-0 v Canvey IslandCanvey Island 0-1 Cheshunt | Isthmian League - Premier Division |
| 33 | Sat 1 Feb | 190-1 v Hashtag UnitedHashtag United 1-0 Cheshunt | Isthmian League - Premier Division |
| 34 | Tue 4 Feb | 42-2 v HendonCheshunt 2-2 Hendon | Isthmian League - Premier Division |
| 35 | Sat 8 Feb | 42-1 v Hastings UnitedCheshunt 2-1 Hastings United | Isthmian League - Premier Division |
| 36 | Sat 15 Feb | 181-2 v Cray WanderersCray Wanderers 2-1 Cheshunt | Isthmian League - Premier Division |
| 37 | Sat 22 Feb | 43-0 v DartfordCheshunt 3-0 Dartford | Isthmian League - Premier Division |
| 38 | Sat 8 Mar | 10 0-1 v Carshalton AthleticCheshunt 0-1 Carshalton Athletic | Isthmian League - Premier Division |
| 39 | Tue 18 Mar | 81-2 v Potters Bar TownCheshunt 1-2 Potters Bar Town | Hertfordshire County Cup Semi Final |
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