| 1 | 3/8/2019 | 53-1 v TilburyCray Valley PM 3-1 Tilbury | Friendly |
| 2 | 6/8/2019 | 53-1 v Grays AthleticCray Valley PM 3-1 Grays Athletic | Friendly |
| 3 | 10/8/2019 | 52-1 v Chatham TownCray Valley PM 2-1 Chatham Town | Emirates FA Cup Extra Preliminary Round |
| 4 | 17/8/2019 | 50-0 v Hastings UnitedCray Valley PM 0-0 Hastings United | BetVictor Isthmian South East Division |
| 5 | 20/8/2019 | 193-1 v SittingbourneSittingbourne 1-3 Cray Valley PM | BetVictor Isthmian South East Division |
| 6 | 24/8/2019 | 50-2 v WhyteleafeCray Valley PM 0-2 Whyteleafe | Emirates FA Cup Preliminary Round |
| 7 | 31/8/2019 | 53-0 v Herne BayHerne Bay 0-3 Cray Valley PM | BetVictor Isthmian South East Division |
| 8 | 3/9/2019 | 5 1-2 v Phoenix SportsCray Valley PM 1-2 Phoenix Sports | Velocity Trophy Group 9 |
| 9 | 17/9/2019 | 5 1-1 v Whitstable TownWhitstable Town 1-1 Cray Valley PM | BetVictor Isthmian South East Division |
| 10 | 28/9/2019 | 52-2 v VCD AthleticVCD Athletic 2-2 Cray Valley PM | Velocity Trophy Group 9 |
| 11 | 1/10/2019 | 51-2 v Whitstable TownCray Valley PM 1-2 Whitstable Town | Kent Senior Cup First Round |
| 12 | 5/10/2019 | 52-1 v Ashford UnitedAshford United 1-2 Cray Valley PM | BetVictor Isthmian South East Division |
| 13 | 12/10/2019 | 52-5 v Maldon & TiptreeMaldon & Tiptree 5-2 Cray Valley PM | Buildbase FA Trophy Preliminary Round |
| 14 | 19/10/2019 | 52-0 v Faversham TownCray Valley PM 2-0 Faversham Town | BetVictor Isthmian South East Division |
| 15 | 26/10/2019 | 53-2 v Burgess Hill TownBurgess Hill Town 2-3 Cray Valley PM | BetVictor Isthmian South East Division |
| 16 | 2/11/2019 | 51-0 v Three BridgesCray Valley PM 1-0 Three Bridges | BetVictor Isthmian South East Division |
| 17 | 9/11/2019 | 52-0 v RamsgateRamsgate 0-2 Cray Valley PM | BetVictor Isthmian South East Division |
| 18 | 16/11/2019 | 51-1 v Hythe TownCray Valley PM 1-1 Hythe Town | BetVictor Isthmian South East Division |
| 19 | 23/11/2019 | 51-1 v GuernseyCray Valley PM 1-1 Guernsey | BetVictor Isthmian South East Division |
| 20 | 7/12/2019 | 53-1 v East Grinstead TownCray Valley PM 3-1 East Grinstead Town | BetVictor Isthmian South East Division |
| 21 | 10/12/2019 | 53-4 v AFC WimbledonCray Valley PM 3-4 AFC Wimbledon | London County Cup Second Round |
| 22 | 14/12/2019 | 50-2 v Phoenix SportsPhoenix Sports 2-0 Cray Valley PM | BetVictor Isthmian South East Division |
| 23 | 1/1/2020 | 51-1 v Sevenoaks TownSevenoaks Town 1-1 Cray Valley PM | BetVictor Isthmian South East Division |
| 24 | 4/1/2020 | 51-2 v Herne BayCray Valley PM 1-2 Herne Bay | BetVictor Isthmian South East Division |
| 25 | 11/1/2020 | 51-3 v Haywards Heath TownHaywards Heath Town 3-1 Cray Valley PM | BetVictor Isthmian South East Division |
| 26 | 18/1/2020 | 50-0 v Faversham TownFaversham Town 0-0 Cray Valley PM | BetVictor Isthmian South East Division |
| 27 | 25/1/2020 | 53-1 v Ashford UnitedCray Valley PM 3-1 Ashford United | BetVictor Isthmian South East Division |
| 28 | 28/1/2020 | 55-0 v VCD AthleticCray Valley PM 5-0 VCD Athletic | BetVictor Isthmian South East Division |
| 29 | 4/2/2020 | 54-3 v Whitstable TownCray Valley PM 4-3 Whitstable Town | BetVictor Isthmian South East Division |
| 30 | 8/2/2020 | 52-0 v Phoenix SportsCray Valley PM 2-0 Phoenix Sports | BetVictor Isthmian South East Division |
| 31 | 22/2/2020 | 51-0 v Burgess Hill TownCray Valley PM 1-0 Burgess Hill Town | BetVictor Isthmian South East Division |
| 32 | 10/3/2020 | 53-2 v WhyteleafeCray Valley PM 3-2 Whyteleafe | BetVictor Isthmian South East Division |
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