| 1 | Tue 17 Sep | 120-0 v Herne BaySheppey United 0-0 Herne Bay | Velocity Cup Second Round |
| 2 | Sat 21 Sep | 12 2-0 v Steyning Town CommunitySheppey United 2-0 Steyning Town Community | Isthmian League - South East Division |
| 3 | Tue 24 Sep | 12 1-1 v Hythe TownSheppey United 1-1 Hythe Town | Kent Senior Cup First Round |
| 4 | Sat 28 Sep | 122-0 v Phoenix SportsPhoenix Sports 0-2 Sheppey United | Isthmian League - South East Division |
| 5 | Sat 12 Oct | 120-5 v RamsgateRamsgate 5-0 Sheppey United | Isthmian League - South East Division |
| 6 | Tue 15 Oct | 121-1 v MersthamMerstham 1-1 Sheppey United | Isthmian League - South East Division |
| 7 | Sat 19 Oct | 122-3 v MargateSheppey United 2-3 Margate | Isthmian League - South East Division |
| 8 | Tue 22 Oct | 12 2-0 v Littlehampton TownSheppey United 2-0 Littlehampton Town | Isthmian League - South East Division |
| 9 | Sat 26 Oct | 124-0 v Herne BayHerne Bay 0-4 Sheppey United | Isthmian League - South East Division |
| 10 | Sat 2 Nov | 120-1 v Beckenham TownSheppey United 0-1 Beckenham Town | Isthmian League - South East Division |
| 11 | Tue 5 Nov | 121-1 v Erith TownErith Town 1-1 Sheppey United | Isthmian League - South East Division |
| 12 | Sat 9 Nov | 124-3 v MersthamSheppey United 4-3 Merstham | Isthmian League - South East Division |
| 13 | Sat 16 Nov | 12 0-3 v Burgess Hill TownBurgess Hill Town 3-0 Sheppey United | Isthmian League - South East Division |
| 14 | Tue 26 Nov | 12 4-2 v MargateMargate 2-4 Sheppey United | Velocity Cup Third Qualifying Round |
| 15 | Sat 30 Nov | 12 1-0 v Eastbourne TownSheppey United 1-0 Eastbourne Town | Isthmian League - South East Division |
| 16 | Sat 21 Dec | 121-3 v Deal TownDeal Town 3-1 Sheppey United | Isthmian League - South East Division |
| 17 | Thu 26 Dec | 120-4 v SittingbourneSittingbourne 4-0 Sheppey United | Isthmian League - South East Division |
| 18 | Wed 1 Jan | 123-1 v Hythe TownSheppey United 3-1 Hythe Town | Isthmian League - South East Division |
| 19 | Tue 14 Jan | 120-1 v Billericay TownBillericay Town 1-0 Sheppey United | Velocity Cup Quarter Final |
| 20 | Sat 18 Jan | 12 3-2 v Broadbridge HeathSheppey United 3-2 Broadbridge Heath | Isthmian League - South East Division |
| 21 | Tue 21 Jan | 122-2 v Burgess Hill TownSheppey United 2-2 Burgess Hill Town | Isthmian League - South East Division |
| 22 | Sat 25 Jan | 122-2 v Eastbourne TownEastbourne Town 2-2 Sheppey United | Isthmian League - South East Division |
| 23 | Sat 1 Feb | 122-1 v LancingSheppey United 2-1 Lancing | Isthmian League - South East Division |
| 24 | Tue 4 Feb | 121-2 v AFC Croydon AthleticAFC Croydon Athletic 2-1 Sheppey United | Isthmian League - South East Division |
| 25 | Sat 8 Feb | 121-3 v Littlehampton TownLittlehampton Town 3-1 Sheppey United | Isthmian League - South East Division |
| 26 | Sat 15 Feb | 120-1 v RamsgateSheppey United 0-1 Ramsgate | Isthmian League - South East Division |
| 27 | Tue 18 Feb | 31-2 v East Grinstead TownEast Grinstead Town 2-1 Sheppey United | Isthmian League - South East Division |
| 28 | Sat 22 Feb | 32-3 v MargateMargate 3-2 Sheppey United | Isthmian League - South East Division |
| 29 | Sat 1 Mar | 30-0 v Herne BaySheppey United 0-0 Herne Bay | Isthmian League - South East Division |
| 30 | Sat 8 Mar | 30-1 v Beckenham TownBeckenham Town 1-0 Sheppey United | Isthmian League - South East Division |
| 31 | Sat 15 Mar | 3 1-2 v Ashford UnitedAshford United 2-1 Sheppey United | Isthmian League - South East Division |
| 32 | Sat 22 Mar | 32-4 v Deal TownSheppey United 2-4 Deal Town | Isthmian League - South East Division |
| 33 | Sat 29 Mar | 3 4-1 v Broadbridge HeathBroadbridge Heath 1-4 Sheppey United | Isthmian League - South East Division |
| 34 | Sat 5 Apr | 3 3-1 v East Grinstead TownSheppey United 3-1 East Grinstead Town | Isthmian League - South East Division |
| 35 | Sat 12 Apr | 31-0 v AFC Croydon AthleticSheppey United 1-0 AFC Croydon Athletic | Isthmian League - South East Division |
| 36 | Fri 18 Apr | 33-2 v Steyning Town CommunitySteyning Town Community 2-3 Sheppey United | Isthmian League - South East Division |
| 37 | Mon 21 Apr | 30-0 v SittingbourneSheppey United 0-0 Sittingbourne | Isthmian League - South East Division |
| 38 | Sat 26 Apr | 30-2 v Sevenoaks TownSevenoaks Town 2-0 Sheppey United | Isthmian League - South East Division |
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