| 1 | Tue 11 Jul | 42-2 v BromleyDulwich Hamlet 2-2 Bromley | Friendly |
| 2 | Sat 15 Jul | 60-0 v AveleyAveley 0-0 Dulwich Hamlet | Friendly |
| 3 | Tue 18 Jul | 193-1 v Welling UnitedWelling United 1-3 Dulwich Hamlet | Friendly |
| 4 | Sat 22 Jul | 122-1 v Erith & BelvedereDulwich Hamlet 2-1 Erith & Belvedere | Friendly |
| 5 | Tue 25 Jul | 181-1 v Tooting & Mitcham UnitedTooting & Mitcham United 1-1 Dulwich Hamlet | Friendly |
| 6 | Fri 28 Jul | 63-1 v MillwallDulwich Hamlet 3-1 Millwall | Friendly |
| 7 | Tue 1 Aug | 122-2 v Welwyn Garden CityWelwyn Garden City 2-2 Dulwich Hamlet | Friendly |
| 8 | Sat 5 Aug | 123-2 v Cray Valley PMCray Valley PM 2-3 Dulwich Hamlet | Friendly |
| 9 | Sat 12 Aug | 122-2 v Hashtag UnitedHashtag United 2-2 Dulwich Hamlet | Isthmian League - Premier Division |
| 10 | Sat 19 Aug | 121-2 v Hastings UnitedDulwich Hamlet 1-2 Hastings United | Isthmian League - Premier Division |
| 11 | Sat 23 Sep | 62-0 v Hartley WintneyCray Valley PM 2-0 Hartley Wintney | Isuzu FA Trophy Second Qualifying Round |
| 12 | Wed 27 Sep | 67-1 v RamsgateRamsgate 1-7 Cray Valley PM | Kent Senior Cup First Round |
| 13 | Sat 30 Sep | 63-3 v Carshalton AthleticCarshalton Athletic 3-3 Cray Valley PM | Emirates FA Cup Third Qualifying Round |
| 14 | Tue 3 Oct | 62-1 v Carshalton AthleticCray Valley PM 2-1 Carshalton Athletic | Emirates FA Cup Third Qualifying Round Replay |
| 15 | Sat 7 Oct | 62-1 v Carshalton AthleticCarshalton Athletic 1-2 Cray Valley PM | Isuzu FA Trophy Third Qualifying Round |
| 16 | Tue 17 Oct | 6 0-3 v Punjab UnitedPunjab United 3-0 Cray Valley PM | Kent Senior Cup Second Round |
| 17 | Tue 24 Oct | 62-2 v Littlehampton TownCray Valley PM 2-2 Littlehampton Town | Isthmian League - South East Division |
| 18 | Sat 28 Oct | 62-0 v Chatham TownChatham Town 0-2 Cray Valley PM | Isuzu FA Trophy First Round |
| 19 | Sun 5 Nov | 61-1 v Charlton AthleticCharlton Athletic 1-1 Cray Valley PM | Emirates FA Cup First Round |
| 20 | Sat 11 Nov | 63-0 v Erith & BelvedereCray Valley PM 3-0 Erith & Belvedere | Isthmian League - South East Division |
| 21 | Wed 15 Nov | 61-6 v Charlton AthleticCray Valley PM 1-6 Charlton Athletic | Emirates FA Cup First Round Replay |
| 22 | Sat 18 Nov | 61-5 v Hampton & Richmond BoroughCray Valley PM 1-5 Hampton & Richmond Borough | Isuzu FA Trophy Second Round |
| 23 | Tue 21 Nov | 64-1 v MersthamCray Valley PM 4-1 Merstham | Isthmian League - South East Division |
| 24 | Sat 2 Dec | 61-0 v Herne BayHerne Bay 0-1 Cray Valley PM | Isthmian League - South East Division |
| 25 | Tue 5 Dec | 62-1 v Beckenham TownCray Valley PM 2-1 Beckenham Town | Isthmian League - South East Division |
| 26 | Tue 26 Dec | 63-1 v Phoenix SportsCray Valley PM 3-1 Phoenix Sports | Isthmian League - South East Division |
| 27 | Sat 30 Dec | 62-2 v SittingbourneCray Valley PM 2-2 Sittingbourne | Isthmian League - South East Division |
| 28 | Mon 1 Jan | 61-0 v Sevenoaks TownSevenoaks Town 0-1 Cray Valley PM | Isthmian League - South East Division |
| 29 | Tue 9 Jan | 61-1 v LancingCray Valley PM 1-1 Lancing | Isthmian League - South East Division |
| 30 | Sat 13 Jan | 63-1 v Sheppey UnitedCray Valley PM 3-1 Sheppey United | Isthmian League - South East Division |
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