| 1 | Tue 29 Aug | 421-1 v Exeter CityExeter City 1-1 Stevenage | Carabao Cup Second Round |
| 2 | Tue 5 Sep | 421-1 v AFC WimbledonAFC Wimbledon 1-1 Stevenage | EFL Trophy |
| 3 | Sat 30 Sep | 72-1 v Dulwich HamletCheshunt 2-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 4 | Sat 7 Oct | 110-1 v Dulwich HamletCheshunt 0-1 Dulwich Hamlet | Isuzu FA Trophy Third Qualifying Round |
| 5 | Sat 14 Oct | 71-2 v Folkestone InvictaFolkestone Invicta 2-1 Cheshunt | Isthmian League - Premier Division |
| 6 | Sat 21 Oct | 100-2 v Haringey BoroughCheshunt 0-2 Haringey Borough | Isthmian League - Premier Division |
| 7 | Tue 24 Oct | 71-1 v Potters Bar TownPotters Bar Town 1-1 Cheshunt | Isthmian League - Premier Division |
| 8 | Sat 11 Nov | 80-6 v HornchurchCheshunt 0-6 Hornchurch | Isthmian League - Premier Division |
| 9 | Tue 21 Nov | 155-4 v KingstonianCheshunt 5-4 Kingstonian | Isthmian League - Premier Division |
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