| 1 | Sat 13 Jul | 11-4 v Faversham TownFaversham Town 4-1 Sheppey United | Friendly |
| 2 | Sat 10 Aug | 12-1 v Three BridgesThree Bridges 1-2 Sheppey United | Isthmian League - South East Division |
| 3 | Sat 17 Aug | 13-0 v North Greenford UnitedNorth Greenford United 0-3 Sheppey United | Emirates FA Cup Preliminary Round |
| 4 | Sat 24 Aug | 13-1 v Sevenoaks TownSheppey United 3-1 Sevenoaks Town | Isthmian League - South East Division |
| 5 | Mon 26 Aug | 14-0 v Hythe TownHythe Town 0-4 Sheppey United | Isthmian League - South East Division |
| 6 | Sat 31 Aug | 11-1 v Hanwell TownSheppey United 1-1 Hanwell Town | Emirates FA Cup First Qualifying Round |
| 7 | Tue 3 Sep | 10-6 v Hanwell TownHanwell Town 6-0 Sheppey United | Emirates FA Cup First Qualifying Round Replay |
| 8 | Sat 7 Sep | 12-3 v RamsgateSheppey United 2-3 Ramsgate | Isuzu FA Trophy First Qualifying Round |
| 9 | Tue 10 Sep | 13-1 v Erith TownSheppey United 3-1 Erith Town | Isthmian League - South East Division |
| 10 | Tue 17 Sep | 10-0 v Herne BaySheppey United 0-0 Herne Bay | Velocity Cup Second Round |
| 11 | Sat 21 Sep | 12-0 v Steyning Town CommunitySheppey United 2-0 Steyning Town Community | Isthmian League - South East Division |
| 12 | Tue 24 Sep | 11-1 v Hythe TownSheppey United 1-1 Hythe Town | Kent Senior Cup First Round |
| 13 | Sat 28 Sep | 12-0 v Phoenix SportsPhoenix Sports 0-2 Sheppey United | Isthmian League - South East Division |
| 14 | Sat 12 Oct | 10-5 v RamsgateRamsgate 5-0 Sheppey United | Isthmian League - South East Division |
| 15 | Tue 15 Oct | 11-1 v MersthamMerstham 1-1 Sheppey United | Isthmian League - South East Division |
| 16 | Sat 19 Oct | 1 2-3 v MargateSheppey United 2-3 Margate | Isthmian League - South East Division |
| 17 | Tue 22 Oct | 1 2-0 v Littlehampton TownSheppey United 2-0 Littlehampton Town | Isthmian League - South East Division |
| 18 | Sat 26 Oct | 14-0 v Herne BayHerne Bay 0-4 Sheppey United | Isthmian League - South East Division |
| 19 | Sat 2 Nov | 10-1 v Beckenham TownSheppey United 0-1 Beckenham Town | Isthmian League - South East Division |
| 20 | Tue 5 Nov | 11-1 v Erith TownErith Town 1-1 Sheppey United | Isthmian League - South East Division |
| 21 | Sat 9 Nov | 14-3 v MersthamSheppey United 4-3 Merstham | Isthmian League - South East Division |
| 22 | Sat 16 Nov | 10-3 v Burgess Hill TownBurgess Hill Town 3-0 Sheppey United | Isthmian League - South East Division |
| 23 | Sat 23 Nov | 13-1 v Phoenix SportsSheppey United 3-1 Phoenix Sports | Isthmian League - South East Division |
| 24 | Tue 26 Nov | 14-2 v MargateMargate 2-4 Sheppey United | Velocity Cup Third Qualifying Round |
| 25 | Sat 30 Nov | 11-0 v Eastbourne TownSheppey United 1-0 Eastbourne Town | Isthmian League - South East Division |
| 26 | Tue 3 Dec | 13-0 v DartfordSheppey United 3-0 Dartford | Velocity Cup Fourth Round |
| 27 | Sat 7 Dec | 10-0 v LancingLancing 0-0 Sheppey United | Isthmian League - South East Division |
| 28 | Sat 14 Dec | 11-2 v Ashford UnitedSheppey United 1-2 Ashford United | Isthmian League - South East Division |
| 29 | Sat 21 Dec | 11-3 v Deal TownDeal Town 3-1 Sheppey United | Isthmian League - South East Division |
| 30 | Thu 26 Dec | 10-4 v SittingbourneSittingbourne 4-0 Sheppey United | Isthmian League - South East Division |
| 31 | Sat 28 Dec | 12-3 v Three BridgesSheppey United 2-3 Three Bridges | Isthmian League - South East Division |
| 32 | Wed 1 Jan | 13-1 v Hythe TownSheppey United 3-1 Hythe Town | Isthmian League - South East Division |
| 33 | Tue 14 Jan | 10-1 v Billericay TownBillericay Town 1-0 Sheppey United | Velocity Cup Quarter Final |
| 34 | Sat 18 Jan | 13-2 v Broadbridge HeathSheppey United 3-2 Broadbridge Heath | Isthmian League - South East Division |
| 35 | Tue 21 Jan | 12-2 v Burgess Hill TownSheppey United 2-2 Burgess Hill Town | Isthmian League - South East Division |
| 36 | Sat 25 Jan | 12-2 v Eastbourne TownEastbourne Town 2-2 Sheppey United | Isthmian League - South East Division |
| 37 | Sat 1 Feb | 12-1 v LancingSheppey United 2-1 Lancing | Isthmian League - South East Division |
| 38 | Tue 4 Feb | 11-2 v AFC Croydon AthleticAFC Croydon Athletic 2-1 Sheppey United | Isthmian League - South East Division |
| 39 | Sat 8 Feb | 1 1-3 v Littlehampton TownLittlehampton Town 3-1 Sheppey United | Isthmian League - South East Division |
| 40 | Sat 15 Feb | 10-1 v RamsgateSheppey United 0-1 Ramsgate | Isthmian League - South East Division |
| 41 | Tue 18 Feb | 1 1-2 v East Grinstead TownEast Grinstead Town 2-1 Sheppey United | Isthmian League - South East Division |
| 42 | Sat 22 Feb | 12-3 v MargateMargate 3-2 Sheppey United | Isthmian League - South East Division |
| 43 | Sat 1 Mar | 10-0 v Herne BaySheppey United 0-0 Herne Bay | Isthmian League - South East Division |
| 44 | Sat 8 Mar | 10-1 v Beckenham TownBeckenham Town 1-0 Sheppey United | Isthmian League - South East Division |
| 45 | Sat 15 Mar | 1 1-2 v Ashford UnitedAshford United 2-1 Sheppey United | Isthmian League - South East Division |
| 46 | Sat 29 Mar | 14-1 v Broadbridge HeathBroadbridge Heath 1-4 Sheppey United | Isthmian League - South East Division |
| 47 | Sat 5 Apr | 13-1 v East Grinstead TownSheppey United 3-1 East Grinstead Town | Isthmian League - South East Division |
| 48 | Sat 12 Apr | 11-0 v AFC Croydon AthleticSheppey United 1-0 AFC Croydon Athletic | Isthmian League - South East Division |
| 49 | Fri 18 Apr | 13-2 v Steyning Town CommunitySteyning Town Community 2-3 Sheppey United | Isthmian League - South East Division |
| 50 | Mon 21 Apr | 10-0 v SittingbourneSheppey United 0-0 Sittingbourne | Isthmian League - South East Division |
| 51 | Sat 26 Apr | 10-2 v Sevenoaks TownSevenoaks Town 2-0 Sheppey United | Isthmian League - South East Division |
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