| 1 | Wed 2 Jul | 31-3 v Whitstable TownSheppey Sports 1-3 Whitstable Town | Friendly |
| 2 | Sat 26 Jul | 134-1 v Borden VillageBorden Village 1-4 Sheppey Sports | Friendly |
| 3 | Sat 9 Aug | 31-3 v AFC Greenwich BoroughAFC Greenwich Borough 3-1 Sheppey Sports | Southern Counties East League First Division |
| 4 | Sat 23 Aug | 30-4 v Soul Tower HamletsSoul Tower Hamlets 4-0 Sheppey Sports | Isuzu FA Vase First Qualifying Round |
| 5 | Mon 25 Aug | 31-1 v Lordswood AFCLordswood AFC 1-1 Sheppey Sports | Southern Counties East League First Division |
| 6 | Sat 30 Aug | 30-0 v SC ThamesmeadSheppey Sports 0-0 SC Thamesmead | Southern Counties East League First Division |
| 7 | Mon 1 Sep | 3 0-3 v GreenwaysSheppey Sports 0-3 Greenways | Southern Counties East League First Division |
| 8 | Sat 13 Sep | 30-2 v Lewisham BoroughSheppey Sports 0-2 Lewisham Borough | Southern Counties East League First Division |
| 9 | Sat 20 Sep | 32-0 v Banstead AthleticBanstead Athletic 0-2 Sheppey Sports | Southern Counties East League First Division |
| 10 | Sat 27 Sep | 32-2 v Welling TownWelling Town 2-2 Sheppey Sports | Southern Counties East League First Division |
| 11 | Sat 4 Oct | 30-4 v Lordswood AFCSheppey Sports 0-4 Lordswood AFC | Southern Counties East League First Division |
| 12 | Sat 25 Oct | 31-2 v Halls AFCHalls AFC 2-1 Sheppey Sports | Southern Counties East League First Division |
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