Isthmian League South East Division
| Date | Fixture | ||||||
| 06/07 | FRD | Glebe | 0 | v | 3 | Cray Valley | |
| 09/07 | FRD | FC Elmstead | 2 | v | 2 | Cray Valley |  |
| 15/07 | FRD | Carshalton Athletic | 0 | v | 0 | Cray Valley | |
| 20/07 | FRD | Hailsham Town | 0 | v | 10 | Cray Valley | |
| 23/07 | FRD | Welling Town | 0 | v | 3 | Cray Valley | |
| 27/07 | RVC | Chatham Town | 0 | v | 1 | Cray Valley | |
| 03/08 | FRD | Cray Valley | 3 | v | 1 | Tilbury | |
| 06/08 | FRD | Cray Valley | 3 | v | 1 | Grays Athletic | |
| 10/08 | FAC | Cray Valley | 2 | v | 1 | Chatham Town | |
| 17/08 | BVL | Cray Valley | 0 | v | 0 | Hastings Utd | |
| 20/08 | BVL | Sittingbourne | 1 | v | 3 | Cray Valley | |
| 24/08 | FAC | Cray Valley | 0 | v | 2 | Whyteleafe | |
| 26/08 | BVL | Cray Valley | 1 | v | 0 | Sevenoaks Town | |
| 31/08 | BVL | Herne Bay | 0 | v | 3 | Cray Valley | |
| 03/09 | VT | Cray Valley | 1 | v | 2 | Phoenix Sports | |
| 14/09 | BVL | Cray Valley | 0 | v | 2 | Chichester City | |
| 17/09 | BVL | Whitstable Town | 1 | v | 1 | Cray Valley | |
| 28/09 | VT | VCD | 2 | v | 2 | Cray Valley (Pens 6-7) | |
| 01/10 | KSC | Cray Valley | 1 | v | 2 | Whitstable Town | |
| 05/10 | BVL | Ashford Utd | 1 | v | 2 | Cray Valley | |
| 08/10 | VT | Cray Valley | 0 | v | 1 | Sevenoaks Town | |
| 12/10 | FAT | Maldon & Tiptree | 5 | v | 2 | Cray Valley | |
| 19/10 | BVL | Cray Valley | 2 | v | 0 | Faversham Town | |
| 26/10 | BVL | Burgess Hill Town | 2 | v | 3 | Cray Valley | |
| 02/11 | BVL | Cray Valley | 1 | v | 0 | Three Bridges | |
| 05/11 | VT | Sittingbourne | 3 | v | 2 | Cray Valley | |
| 09/11 | BVL | Ramsgate | 0 | v | 2 | Cray Valley | |
| 16/11 | BVL | Cray Valley | 1 | v | 1 | Hythe Town | |
| 23/11 | BVL | Cray Valley | 1 | v | 1 | Guernsey | |
| 30/11 | BVL | Whitehawk | 2 | v | 0 | Cray Valley | |
| 07/12 | BVL | Cray Valley | 3 | v | 1 | East Grinstead Town | |
| 10/12 | LSC | Cray Valley | 3 | v | 4 | AFC Wimbledon | |
| 14/12 | BVL | Phoenix Sports | 2 | v | 0 | Cray Valley | |
| 01/01/2020 | BVL | Sevenoaks Town | 1 | v | 1 | Cray Valley | |
| 04/01 | BVL | Cray Valley | 1 | v | 2 | Herne Bay | |
| 11/01 | BVL | Haywards Heath Town | 3 | v | 1 | Cray Valley | |
| 18/01 | BVL | Faversham Town | 0 | v | 0 | Cray Valley | |
| 25/01 | BVL | Cray Valley | 3 | v | 1 | Ashford Utd | |
| 28/01 | BVL | Cray Valley | 5 | v | 0 | VCD Athletic | |
| 01/02 | BVL | Whyteleafe | 0 | v | 4 | Cray Valley | |
| 04/02 | BVL | Cray Valley | 4 | v | 3 | Whitstable Town | |
| 08/02 | BVL | Cray Valley | 2 | v | 0 | Phoenix Sports | |
| 22/02 | BVL | Cray Valley | 1 | v | 0 | Burgess Hill Town | |
| 07/03 | BVL | Cray Valley | 5 | v | 3 | Ramsgate | |
| 10/03 | BVL | Cray Valley | 3 | v | 2 | Whyteleafe | |
| 21/03 | BVL | Chichester City | v | Cray Valley | |||
| 28/03 | BVL | Cray Valley | v | Haywards Heath Town | |||
| 31/03 | BVL | Three Bridges | v | Cray Valley | |||
| 04/04 | BVL | Hastings Utd | v | Cray Valley | |||
| 11/04 | BVL | Cray Valley | v | Sittingbourne | |||
| 13/04 | BVL | VCD Athletic | v | Cray Valley | |||
| 19/04 | BVL | Guernsey | v | Cray Valley | |||
| 25/04 | BVL | Cray Valley | v | Whitehawk |
| FAC=FA Cup | LSC=London Senior Cup | |
| KSC=Kent Senior Cup | FRD=Friendly | VT=Velocity Trophy |
| BVL=The Bet Victor Football League | RVC=Roy Vinter Challenge Shield | FAT=FA Trophy |
Bluefin Insurance U23 Development League
| Date | Fixture | ||||||
| 06/07 | FRD | Meridian VP | 2 | v | 0 | Cray Valley | |
| 13/07 | FRD | Tudor Sports | 2 | v | 1 | Cray Valley | |
| 20/07 | FRD | Red Velvet | 5 | v | 4 | Cray Valley | |
| 31/07 | FRD | Phoenix Academy | 5 | v | 1 | Cray Valley | |
| 01/08 | FRD | Farnborough OBG | 5 | v | 3 | Cray Valley | |
| 03/08 | FRD | Phoenix U23 | 2 | v | 1 | Cray Valley | |
| 13/08 | FRD | Faversham U23 | 4 | v | 0 | Cray Valley | |
| 02/09 | FAY | Cray Valley | 2 | v | 1 | Bridon Ropes | |
| 04/09 | DEV | Ware | 4 | v | 1 | Cray Valley | |
| 12/09 | DEV | Cray Valley | 0 | v | 0 | Witham Town | |
| 18/09 | FAY | Dulwich Hamlet | 1 | v | 0 | Cray Valley | |
| 10/10 | DEV | Barking | 2 | v | 3 | Cray Valley | |
| 17/10 | DEV | Cray Valley | 4 | v | 2 | Hertford Town | |
| 28/10 | DEV | Haringey Borough | 7 | v | 0 | Cray Valley | |
| 07/11 | DEV | Cray Valley | 0 | v | 11 | Aveley | |
| 14/11 | DEV | Cray Valley | 3 | v | 2 | Enfield Town | |
| 18/11 | DEV | Bowers & Pitsea | 8 | v | 1 | Cray Valley | |
| 21/11 | KIC | Cray Valley | 2 | v | 1 | West Wickham | |
| 09/01 | KIC | Cray Valley | 1 | v | 2 | H&B Res | |
| 16/01 | DEV | Cray Valley | 2 | v | 7 | Haringey Borough | |
| 29/01 | DEV | Enfield Town | 2 | v | 1 | Cray Valley | |
| 05/02 | DEV | Witham Town | 2 | v | 1 | Cray Valley | |
| 12/02 | KIC | Whitstable Res | 2 | v | 0 | Cray Valley | |
| 27/02 | DEV | Cray Valley | 1 | v | 2 | Ware | |
| 04/03 | PC | Cray Valley | 3 | v | 1 | Folkestone Invicta | |
| 12/03 | DEV | Cray Valley | 3 | v | 4 | Barking | |
| 19/03 | DEV | Cray Valley | v | Bowers & Pitsea | |||
| 26/03 | DEV | Cray Valley | v | Bury Town | |||
| 02/04 | DEV | Hertford Town | v | Cray Valley | |||
| 20/04 | DEV | Aveley | v | Cray Valley |
| KIC=Kent Intermediate Cup | PC=Presidents Cup | FRD=Friendly |
| DEV=Isthmian Development League | FAY=FA Youth Cup |
Kent Youth League U15N Team
| Date | Fixture | ||||||
| 08/09 | KYL | Cray Valley | 5 | v | 2 | Bridon Ropes | |
| 22/09 | KYL | Cray Valley | 3 | v | 2 | Bromley | |
| 29/09 | KYC | Cray Valley | 3 | v | 2 | Ebbsfleet Utd | |
| 06/10 | KYL | Cray Valley | 13 | v | 0 | Danson Sports | |
| 13/10 | LC | Cray Valley | 5 | v | 1 | Phoenix Sports | |
| 20/10 | KYL | Kent Football Utd | 3 | v | 5 | Cray Valley | |
| 03/11 | KYL | Cray Valley | 5 | v | 3 | Cray Wanderers | |
| 17/11 | LC | Ramsgate | 2 | v | 10 | Cray Valley | |
| 01/12 | LC | Cray Valley | 2 | v | 3 | Welling Utd | |
| 08/12 | KYL | Cray Valley | 0 | v | 3 | Phoenix Sports | |
| 15/12 | KYC | Cray Valley | 4 | v | 3 | Maidstone Utd | |
| 12/01/2020 | KYL | Cray Valley | 6 | v | 0 | AFC Mottingham | |
| 19/01 | KYL | Bridon Ropes | 2 | v | 4 | Cray Valley | |
| 26/01 | KYC | Bromley | 4 | v | 2 | Cray Valley | |
| 02/02 | KYL | Danson Sports | 0 | v | 8 | Cray Valley | |
| 16/02 | KYL | Cray Wanderers | 1 | v | 9 | Cray Valley | |
| 23/02 | KYL | Cray Valley | 10 | v | 0 | Kent Football Utd | |
| 01/03 | KYL | Cray Valley | 11 | v | 0 | Greenaway Aces | |
| 15/03 | KYL | Phoenix | 2 | v | 5 | Cray Valley | |
| 22/03 | KYL | Mottingham | v | Cray Valley | |||
| 29/03 | FRD | Erith Town | v | Cray Valley | |||
| 05/04 | KYL | Lewisham Borough | v | Cray Valley | |||
| 19/04 | KYL | Bromley | v | Cray Valley | |||
| 26/04 | KYL | Greenways | v | Cray Valley | |||
| 03/05 | KYL | Glebe | v | Cray Valley |
| KYL=Kent Youth League | KYC=Kent Youth Cup | FRD=Friendly |
| LC=League Cup |
Kent Youth League U14N Team
| Date | Fixture | ||||||
| 08/09 | KYL | Danson Sports | 2 | v | 0 | Cray Valley | |
| 15/09 | KYL | Cray Valley | 4 | v | 0 | Bridon Ropes | |
| 22/09 | KYL | Bromley | 1 | v | 2 | Cray Valley | |
| 29/09 | LC | Sittingbourne | 0 | v | 10 | Cray Valley | |
| 06/10 | KYC | Cray Valley | 9 | v | 1 | Chipstead | |
| 13/10 | KYL | Glebe | 2 | v | 1 | Cray Valley | |
| 20/10 | KYL | Long Lane | 4 | v | 1 | Cray Valley | |
| 27/10 | KYL | Cray Valley | 4 | v | 2 | Metrogas | |
| 03/11 | KYC | Cray Valley | 2 | v | 0 | Dover Ath | |
| 10/11 | KYL | Cray Valley | 5 | v | 0 | Tonbridge Angels | |
| 01/12 | KYC | Cray Valley | 1 | v | 2 | Ebbsfleet | |
| 08/12 | KYL | Bridon Ropes | 1 | v | 0 | Cray Valley | |
| 15/12 | KYL | Cray Valley | 5 | v | 0 | Danson Sports | |
| 05/01/2020 | KYL | Metrogas | 1 | v | 2 | Cray Valley | |
| 12/01 | LC | Kent Football Utd | 1 | v | 0 | Cray Valley | |
| 19/01 | KYL | Cray Valley | 8 | v | 3 | AFC Mottingham | |
| 02/02 | KYL | Cray Valley | 7 | v | 2 | West Wickham | |
| 23/02 | KYL | Cray Valley | 4 | v | 1 | Red Devils | |
| 08/03 | KYL | Cray Valley | 5 | v | 1 | Long Lane | |
| 15/03 | KYL | Red Devils | 0 | v | 3 | Cray Valley | |
| 22/03 | KYL | Tonbridge | v | Cray Valley | |||
| 29/04 | KYL | Cray Valley | v | Glebe | |||
| 19/04 | KYL | Mottingham | v | Cray Valley | |||
| 26/04 | KYL | Cray Valley | v | Bromley | |||
| 03/05 | KYL | W Wickham | v | Cray Valley | |||
| 10/05 | KYL | Cray Valley | v | Welling | |||
| 10/05 | KYL | Welling | v | Cray Valley | |||
| 17/05 | KYL | Cray Valley | v | Phoenix | |||
| 17/05 | KYL | Phoenix | v | Cray Valley |
| KYL=Kent Youth League | KYC=Kent Youth Cup | FRD=Friendly |
| LC=League Cup |
Kent Youth League U13s Team
| Date | Fixture | ||||||
| 08/09 | KYL | Bromley | 7 | v | 1 | Cray Valley | |
| 15/09 | KYL | Cray Valley | 4 | v | 2 | Danson Sports | |
| 22/09 | KYL | Cray Valley | 2 | v | 9 | Cray Wanderers | |
| 29/09 | KYL | Metrogas | 3 | v | 1 | Cray Valley | |
| 13/10 | KYC | Cray Valley | 1 | v | 8 | Maidstone Utd | |
| 20/10 | KYL | Cray Valley | 8 | v | 1 | Danson Sports | |
| 17/11 | KYL | Sevenoaks Town | 1 | v | 3 | Cray Valley | |
| 24/11 | KYL | Dulwich | 1 | v | 1 | Cray Valley | |
| 01/12 | KYL | Cray Valley | 2 | v | 1 | Dartford | |
| 08/12 | KYL | Cray Valley | 4 | v | 2 | Erith Town | |
| 05/01/2020 | KYL | Phoenix Sports | 0 | v | 6 | Cray Valley | |
| 12/01 | LC | Cray Valley | 2 | v | 0 | Folkestone Invicta | |
| 19/01 | LC | Cray Wanderers | 2 | v | 1 | Cray Valley | |
| 26/01 | LC | Cray Wanderers | 2 | v | 1 | Cray Valley | |
| 23/02 | KYL | Danson Sports | 0 | v | 8 | Cray Valley | |
| 01/03 | KYL | Erith Town | 1 | v | 6 | Cray Valley | |
| 08/03 | KYL | Cray Valley | 2 | v | 1 | Welling Utd | |
| 08/03 | KYL | Welling Utd | 1 | v | 1 | Cray Valley | |
| 22/03 | KYL | Cray Valley | v | Dulwich Village | |||
| 29/03 | KYL | Red Devils | v | Cray Valley | |||
| 05/04 | KYL | Cray Valley | v | Erith & Belvedere | |||
| 19/04 | KYL | Cray Valley | v | Bromley | |||
| 21/04 | KYL | Cray Wanderers | v | Cray Valley | |||
| 26/04 | KYL | Cray Valley | v | Stansfeld | |||
| 03/05 | KYL | Dartford | v | Cray Valley | |||
| 10/05 | KYL | Gravesham | v | Cray Valley | |||
| 17/05 | KYL | Cray Valley | v | Red Devils | |||
| 24/05 | KYL | Erith & Belvedere | v | Cray Valley |
| KYL=Kent Youth League | KYC=Kent Youth Cup | FRD=Friendly |
| LC=League Cup |
SELKENT U13s D Division
| Date | Fixture | ||||||
| 22/09 | SELKENT | Cray Valley | 8 | v | 2 | Dulwich Utd | |
| 29/09 | SELKENT | Baldon Sports | 2 | v | 2 | Cray Valley | |
| 06/10 | KYC | Cray Valley | 2 | v | 7 | Medway Utd | |
| 13/10 | SELKENT | Eltham Town | 10 | v | 2 | Cray Valley | |
| 20/10 | SELKENT | Cray Valley | 3 | v | 5 | AFC Unity | |
| 03/11 | SELKENT | Baldon Sports | 13 | v | 3 | Cray Valley | |
| 17/11 | SELKENT | Cray Valley | 3 | v | 3 | Eversley Rangers | |
| 24/11 | SELKENT | Dulwich Utd | 4 | v | 2 | Cray Valley | |
| 01/12 | SELKENT | Cray Valley | 1 | v | 6 | Beacons | |
| 08/12 | SELKENT | Orpington | 1 | v | 2 | Cray Valley | |
| 05/01/2020 | SELKENT | Unity | 4 | v | 3 | Cray Valley | |
| 12/01 | SELKENT | Cray Valley | 2 | v | 4 | Baldon Sports | |
| 19/01 | SELKENT | VCD | 4 | v | 5 | Cray Valley | |
| 26/01 | SELKENT | Swanscombe | 1 | v | 4 | Cray Valley | |
| 23/02 | SELKENT | Cray Valley | 2 | v | 6 | Orpington | |
| 08/03 | SELKENT | VCD | 3 | v | 3 | Cray Valley | |
| 15/03 | SELKENT | Dulwich | 5 | v | 0 | Cray Valley |
| SELKENT=League | SC=SELKENT Cup |
| FRD=Friendly | KYC=Kent Youth Cup |
Ladies Team
| Date | Fixture | ||||||
| 15/09 | KWC | Ashford | 4 | v | 0 | Cray Valley | |
| 22/09 | SECWFL | Long Lane | 2 | v | 2 | Cray Valley | |
| 13/10 | SECWFL | Cray Valley | 0 | v | 2 | Maidstone | |
| 20/10 | KWP | Cray Valley | 3 | v | 0 | Meridian Ladies | |
| 27/10 | SECWFL | Margate | 3 | v | 1 | Cray Valley | |
| 03/11 | LC | Cray Valley | 4 | v | 0 | Milford | |
| 10/11 | SECWFL | Cray Valley | 5 | v | 0 | Ramsgate | |
| 17/11 | SECWFL | Canterbury City | 3 | v | 5 | Cray Valley | |
| 24/11 | SECWFL | Meridian | 4 | v | 0 | Cray Valley | |
| 08/12 | SECWFL | Cray Valley | 1 | v | 3 | Bexhill | |
| 15/12 | SECWFL | Maidstone | 5 | v | 0 | Cray Valley | |
| 05/01/2020 | SECWFL | Sittingbourne | 1 | v | 2 | Cray Valley | |
| 19/01 | KWP | Margate | 4 | v | 0 | Cray Valley | |
| 02/02 | SECWFL | Ramsgate | 4 | v | 5 | Cray Valley | |
| 23/02 | SECWFL | Cray Valley | 5 | v | 2 | Long Lane | |
| 15/03 | SECWFL | Cray Valley | 4 | v | 0 | Glebe | |
| 22/03 | SECWFL | Cray Valley | v | Sittingbourne | |||
| 05/04 | SECWFL | Glebe | v | Cray Valley | |||
| 19/04 | SECWFL | Cray Valley | v | Margate | |||
| 03/05 | SECWFL | Cray Valley | v | Meridian |
| KWC=Kent Womens Cup | LC=League Cup | KWP=Kent Womens Plate |
| CC=Chairmans Cup | FRD=Friendly | WFAC=Womens FA Cup |
| SECWFL=League |