| 1 | Sat 10 Aug | 162-1 v Three BridgesThree Bridges 1-2 Sheppey United | Isthmian League - South East Division |
| 2 | Sat 7 Sep | 162-3 v RamsgateSheppey United 2-3 Ramsgate | Isuzu FA Trophy First Qualifying Round |
| 3 | Tue 10 Sep | 163-1 v Erith TownSheppey United 3-1 Erith Town | Isthmian League - South East Division |
| 4 | Sat 21 Sep | 202-0 v Steyning Town CommunitySheppey United 2-0 Steyning Town Community | Isthmian League - South East Division |
| 5 | Tue 24 Sep | 201-1 v Hythe TownSheppey United 1-1 Hythe Town | Kent Senior Cup First Round |
| 6 | Sat 14 Dec | 201-2 v Ashford UnitedSheppey United 1-2 Ashford United | Isthmian League - South East Division |
| 7 | Sat 21 Dec | 20 1-3 v Deal TownDeal Town 3-1 Sheppey United | Isthmian League - South East Division |
| 8 | Thu 26 Dec | 200-4 v SittingbourneSittingbourne 4-0 Sheppey United | Isthmian League - South East Division |
| 9 | Sat 28 Dec | 202-3 v Three BridgesSheppey United 2-3 Three Bridges | Isthmian League - South East Division |
| 10 | Tue 14 Jan | 200-1 v Billericay TownBillericay Town 1-0 Sheppey United | Velocity Cup Quarter Final |
| 11 | Sat 18 Jan | 203-2 v Broadbridge HeathSheppey United 3-2 Broadbridge Heath | Isthmian League - South East Division |
| 12 | Tue 21 Jan | 202-2 v Burgess Hill TownSheppey United 2-2 Burgess Hill Town | Isthmian League - South East Division |
| 13 | Sat 25 Jan | 202-2 v Eastbourne TownEastbourne Town 2-2 Sheppey United | Isthmian League - South East Division |
| 14 | Sat 1 Feb | 202-1 v LancingSheppey United 2-1 Lancing | Isthmian League - South East Division |
| 15 | Tue 4 Feb | 201-2 v AFC Croydon AthleticAFC Croydon Athletic 2-1 Sheppey United | Isthmian League - South East Division |
| 16 | Sat 8 Feb | 201-3 v Littlehampton TownLittlehampton Town 3-1 Sheppey United | Isthmian League - South East Division |
| 17 | Sat 15 Feb | 200-1 v RamsgateSheppey United 0-1 Ramsgate | Isthmian League - South East Division |
| 18 | Tue 18 Feb | 201-2 v East Grinstead TownEast Grinstead Town 2-1 Sheppey United | Isthmian League - South East Division |
| 19 | Sat 22 Feb | 202-3 v MargateMargate 3-2 Sheppey United | Isthmian League - South East Division |
| 20 | Sat 8 Mar | 200-1 v Beckenham TownBeckenham Town 1-0 Sheppey United | Isthmian League - South East Division |
| 21 | Sat 15 Mar | 201-2 v Ashford UnitedAshford United 2-1 Sheppey United | Isthmian League - South East Division |
| 22 | Sat 22 Mar | 20 2-4 v Deal TownSheppey United 2-4 Deal Town | Isthmian League - South East Division |
| 23 | Sat 29 Mar | 204-1 v Broadbridge HeathBroadbridge Heath 1-4 Sheppey United | Isthmian League - South East Division |
| 24 | Sat 5 Apr | 203-1 v East Grinstead TownSheppey United 3-1 East Grinstead Town | Isthmian League - South East Division |
| 25 | Sat 12 Apr | 201-0 v AFC Croydon AthleticSheppey United 1-0 AFC Croydon Athletic | Isthmian League - South East Division |
| 26 | Mon 21 Apr | 200-0 v SittingbourneSheppey United 0-0 Sittingbourne | Isthmian League - South East Division |
| 27 | Sat 26 Apr | 200-2 v Sevenoaks TownSevenoaks Town 2-0 Sheppey United | Isthmian League - South East Division |
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