| 1 | 20/10/2018 | 20-1 v Sevenoaks TownSevenoaks Town 1-0 Ashford United | Bostik League South East Division |
| 2 | 3/11/2018 | 22-3 v HorshamAshford United 2-3 Horsham | Bostik League South East Division |
| 3 | 10/11/2018 | 2 2-1 v East Grinstead TownEast Grinstead Town 1-2 Ashford United | Bostik League South East Division |
| 4 | 13/11/2018 | 23-0 v Greenwich BoroughGreenwich Borough 0-3 Ashford United | Bostik League South East Division |
| 5 | 24/11/2018 | 24-1 v Herne BayAshford United 4-1 Herne Bay | Bostik League South East Division |
| 6 | 1/12/2018 | 22-1 v Phoenix SportsPhoenix Sports 1-2 Ashford United | Bostik League South East Division |
| 7 | 8/12/2018 | 20-0 v WhyteleafeAshford United 0-0 Whyteleafe | Bostik League South East Division |
| 8 | 15/12/2018 | 23-1 v RamsgateRamsgate 1-3 Ashford United | Bostik League South East Division |
| 9 | 26/12/2018 | 24-0 v Faversham TownFaversham Town 0-4 Ashford United | Bostik League South East Division |
| 10 | 1/1/2019 | 20-2 v Hastings UnitedAshford United 0-2 Hastings United | Bostik League South East Division |
| 11 | 5/1/2019 | 24-0 v VCD AthleticVCD Athletic 0-4 Ashford United | Bostik League South East Division |
| 12 | 12/1/2019 | 22-0 v Whitstable TownAshford United 2-0 Whitstable Town | Bostik League South East Division |
| 13 | 19/1/2019 | 27-0 v Greenwich BoroughAshford United 7-0 Greenwich Borough | Bostik League South East Division |
| 14 | 26/1/2019 | 21-0 v Three BridgesThree Bridges 0-1 Ashford United | Bostik League South East Division |
| 15 | 2/2/2019 | 22-1 v Sevenoaks TownAshford United 2-1 Sevenoaks Town | Bostik League South East Division |
| 16 | 5/2/2019 | 22-0 v SittingbourneSittingbourne 0-2 Ashford United | Bostik League South East Division |
| 17 | 16/2/2019 | 21-2 v Herne BayHerne Bay 2-1 Ashford United | Bostik League South East Division |
| 18 | 23/2/2019 | 20-2 v Phoenix SportsAshford United 0-2 Phoenix Sports | Bostik League South East Division |
| 19 | 2/3/2019 | 2 3-1 v WhyteleafeWhyteleafe 1-3 Ashford United | Bostik League South East Division |
| 20 | 9/3/2019 | 23-0 v RamsgateAshford United 3-0 Ramsgate | Bostik League South East Division |
| 21 | 16/3/2019 | 21-0 v East Grinstead TownAshford United 1-0 East Grinstead Town | Bostik League South East Division |
| 22 | 23/3/2019 | 20-0 v HorshamHorsham 0-0 Ashford United | Bostik League South East Division |
| 23 | 30/3/2019 | 23-0 v GuernseyAshford United 3-0 Guernsey | Bostik League South East Division |
| 24 | 6/4/2019 | 21-3 v Hythe TownHythe Town 3-1 Ashford United | Bostik League South East Division |
| 25 | 13/4/2019 | 2 1-3 v Cray WanderersCray Wanderers 3-1 Ashford United | Bostik League South East Division |
| 26 | 19/4/2019 | 23-1 v VCD AthleticAshford United 3-1 VCD Athletic | Bostik League South East Division |
| 27 | 22/4/2019 | 2 2-2 v Hastings UnitedHastings United 2-2 Ashford United | Bostik League South East Division |
| 28 | 27/4/2019 | 25-0 v Haywards Heath TownAshford United 5-0 Haywards Heath Town | Bostik League South East Division |
| 29 | 29/4/2019 | 23-2 v Hastings UnitedHastings United 2-3 Ashford United | Bostik League South East Division Play-off Semi Final |
| 30 | 3/5/2019 | 21-2 v HorshamHorsham 2-1 Ashford United | Bostik League South East Division Play-off Final |
