| 1 | 28/9/2019 | 17 2-2 v VCD AthleticVCD Athletic 2-2 Cray Valley PM | Velocity Trophy Group 9 |
| 2 | 1/10/2019 | 171-2 v Whitstable TownCray Valley PM 1-2 Whitstable Town | Kent Senior Cup First Round |
| 3 | 8/10/2019 | 170-1 v Sevenoaks TownCray Valley PM 0-1 Sevenoaks Town | Velocity Trophy Group 9 |
| 4 | 12/10/2019 | 172-5 v Maldon & TiptreeMaldon & Tiptree 5-2 Cray Valley PM | Buildbase FA Trophy Preliminary Round |
| 5 | 19/10/2019 | 172-0 v Faversham TownCray Valley PM 2-0 Faversham Town | BetVictor Isthmian South East Division |
| 6 | 26/10/2019 | 173-2 v Burgess Hill TownBurgess Hill Town 2-3 Cray Valley PM | BetVictor Isthmian South East Division |
| 7 | 2/11/2019 | 171-0 v Three BridgesCray Valley PM 1-0 Three Bridges | BetVictor Isthmian South East Division |
| 8 | 9/11/2019 | 17 2-0 v RamsgateRamsgate 0-2 Cray Valley PM | BetVictor Isthmian South East Division |
| 9 | 16/11/2019 | 171-1 v Hythe TownCray Valley PM 1-1 Hythe Town | BetVictor Isthmian South East Division |
| 10 | 30/11/2019 | 170-2 v WhitehawkWhitehawk 2-0 Cray Valley PM | BetVictor Isthmian South East Division |
| 11 | 7/12/2019 | 173-1 v East Grinstead TownCray Valley PM 3-1 East Grinstead Town | BetVictor Isthmian South East Division |
| 12 | 10/12/2019 | 173-4 v AFC WimbledonCray Valley PM 3-4 AFC Wimbledon | London County Cup Second Round |
| 13 | 14/12/2019 | 170-2 v Phoenix SportsPhoenix Sports 2-0 Cray Valley PM | BetVictor Isthmian South East Division |
| 14 | 4/1/2020 | 171-2 v Herne BayCray Valley PM 1-2 Herne Bay | BetVictor Isthmian South East Division |
| 15 | 11/1/2020 | 17 1-3 v Haywards Heath TownHaywards Heath Town 3-1 Cray Valley PM | BetVictor Isthmian South East Division |
| 16 | 18/1/2020 | 170-0 v Faversham TownFaversham Town 0-0 Cray Valley PM | BetVictor Isthmian South East Division |
| 17 | 25/1/2020 | 173-1 v Ashford UnitedCray Valley PM 3-1 Ashford United | BetVictor Isthmian South East Division |
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