| 1 | Tue 18 Jul | 173-1 v Welling UnitedWelling United 1-3 Dulwich Hamlet | Friendly |
| 2 | Sat 22 Jul | 40 2-1 v Erith & BelvedereDulwich Hamlet 2-1 Erith & Belvedere | Friendly |
| 3 | Sat 5 Aug | 23-2 v Cray Valley PMCray Valley PM 2-3 Dulwich Hamlet | Friendly |
| 4 | Tue 15 Aug | 17 4-1 v Canvey IslandDulwich Hamlet 4-1 Canvey Island | Isthmian League - Premier Division |
| 5 | Sat 19 Aug | 17 1-2 v Hastings UnitedDulwich Hamlet 1-2 Hastings United | Isthmian League - Premier Division |
| 6 | Sat 26 Aug | 172-3 v HorshamHorsham 3-2 Dulwich Hamlet | Isthmian League - Premier Division |
| 7 | Mon 28 Aug | 122-5 v Chatham TownDulwich Hamlet 2-5 Chatham Town | Isthmian League - Premier Division |
| 8 | Sat 2 Sep | 121-1 v Haringey BoroughDulwich Hamlet 1-1 Haringey Borough | Emirates FA Cup First Qualifying Round |
| 9 | Sat 30 Sep | 21-2 v CheshuntCheshunt 2-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 10 | Sat 7 Oct | 21-0 v CheshuntCheshunt 0-1 Dulwich Hamlet | Isuzu FA Trophy Third Qualifying Round |
| 11 | Tue 10 Oct | 20-3 v Billericay TownBillericay Town 3-0 Dulwich Hamlet | Isthmian League - Premier Division |
| 12 | Sat 14 Oct | 23-2 v KingstonianDulwich Hamlet 3-2 Kingstonian | Isthmian League - Premier Division |
| 13 | Sat 21 Oct | 21-1 v WhitehawkWhitehawk 1-1 Dulwich Hamlet | Isthmian League - Premier Division |
| 14 | Tue 24 Oct | 2 3-2 v Wingate & FinchleyWingate & Finchley 2-3 Dulwich Hamlet | Isthmian League - Premier Division |
| 15 | Sat 28 Oct | 20-2 v LewesDulwich Hamlet 0-2 Lewes | Isuzu FA Trophy First Round |
| 16 | Sat 27 Jan | 25-1 v Canvey IslandChatham Town 5-1 Canvey Island | Isthmian League - Premier Division |
| 17 | Tue 30 Jan | 22-3 v Hashtag UnitedChatham Town 2-3 Hashtag United | Isthmian League - Premier Division |
| 18 | Sat 3 Feb | 22-1 v WhitehawkWhitehawk 1-2 Chatham Town | Isthmian League - Premier Division |
| 19 | Tue 13 Feb | 21-1 v Billericay TownBillericay Town 1-1 Chatham Town | Velocity Cup Quarter Final |
| 20 | Sat 17 Feb | 23-0 v LewesLewes 0-3 Chatham Town | Isthmian League - Premier Division |
| 21 | Tue 20 Feb | 27-2 v Hythe TownChatham Town 7-2 Hythe Town | Kent Senior Cup Quarter Final |
| 22 | Sat 24 Feb | 26-3 v Billericay TownChatham Town 6-3 Billericay Town | Isthmian League - Premier Division |
| 23 | Sat 2 Mar | 20-2 v Carshalton AthleticCarshalton Athletic 2-0 Chatham Town | Isthmian League - Premier Division |
| 24 | Sat 9 Mar | 22-1 v Concord RangersChatham Town 2-1 Concord Rangers | Isthmian League - Premier Division |
| 25 | Tue 12 Mar | 24-2 v Ashford UnitedChatham Town 4-2 Ashford United | Velocity Cup Semi Final |
| 26 | Tue 19 Mar | 23-5 v Ebbsfleet UnitedEbbsfleet United 5-3 Chatham Town | Kent Senior Cup Semi Final |
| 27 | Sat 23 Mar | 2 2-1 v Haringey BoroughChatham Town 2-1 Haringey Borough | Isthmian League - Premier Division |
| 28 | Fri 29 Mar | 22-2 v Cray WanderersCray Wanderers 2-2 Chatham Town | Isthmian League - Premier Division |
| 29 | Wed 17 Apr | 22-1 v Hashtag UnitedChatham Town 2-1 Hashtag United | Velocity Cup Final |
| 30 | Sat 27 Apr | 22-2 v Enfield TownEnfield Town 2-2 Chatham Town | Isthmian League - Premier Division |
| 31 | Wed 1 May | 2 1-1 v HorshamChatham Town 1-1 Horsham | Isthmian League - Premier Division Play-off Semi Final |
| 32 | Mon 6 May | 20-3 v Enfield TownChatham Town 0-3 Enfield Town | Isthmian League - Premier Division Play-off Final |
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