| 1 | Sat 1 Sep 2018 | 11-1 v Brightlingsea RegentCorinthian-Casuals 1-1 Brightlingsea Regent | Bostik League Premier Division |
| 2 | Sat 22 Sep 2018 | 10-5 v Bracknell TownAshford Town (Middx) 0-5 Bracknell Town | Bostik League South Central Division |
| 3 | Tue 25 Sep 2018 | 12-0 v MoleseyMolesey 0-2 Ashford Town (Middx) | Bostik League South Central Division |
| 4 | Sat 29 Sep 2018 | 14-2 v Heybridge SwiftsAshford Town (Middx) 4-2 Heybridge Swifts | Buildbase FA Trophy Extra Preliminary Round |
| 5 | Sat 6 Oct 2018 | 1 1-7 v Hayes & Yeading UnitedHayes & Yeading United 7-1 Ashford Town (Middx) | Bostik League South Central Division |
| 6 | Sat 27 Oct 2018 | 11-2 v LewesAshford Town (Middx) 1-2 Lewes | Buildbase FA Trophy First Qualifying Round |
| 7 | Sat 3 Nov 2018 | 10-3 v NorthwoodNorthwood 3-0 Ashford Town (Middx) | Bostik League South Central Division |
| 8 | Sat 10 Nov 2018 | 12-1 v Waltham AbbeyAshford Town (Middx) 2-1 Waltham Abbey | Bostik League South Central Division |
| 9 | Tue 13 Nov 2018 | 12-1 v FC RomaniaAshford Town (Middx) 2-1 FC Romania | Bostik League South Central Division |
| 10 | Sat 17 Nov 2018 | 12-2 v WareWare 2-2 Ashford Town (Middx) | Bostik League South Central Division |
| 11 | Sat 24 Nov 2018 | 10-3 v MarlowAshford Town (Middx) 0-3 Marlow | Bostik League South Central Division |
| 12 | Sat 12 Jan 2019 | 10-2 v Cray WanderersEast Grinstead Town 0-2 Cray Wanderers | Bostik League South East Division |
| 13 | Sat 19 Jan 2019 | 14-4 v Three BridgesEast Grinstead Town 4-4 Three Bridges | Bostik League South East Division |
| 14 | Tue 22 Jan 2019 | 13-5 v Bognor Regis TownBognor Regis Town 5-3 East Grinstead Town | Sussex County Cup Quarter Final |
| 15 | Sat 26 Jan 2019 | 13-3 v Sevenoaks TownSevenoaks Town 3-3 East Grinstead Town | Bostik League South East Division |
| 16 | Wed 6 Feb 2019 | 15-2 v GuernseyGuernsey 2-5 East Grinstead Town | Bostik League South East Division |
| 17 | Sat 9 Feb 2019 | 11-0 v RamsgateEast Grinstead Town 1-0 Ramsgate | Bostik League South East Division |
| 18 | Sat 16 Feb 2019 | 11-2 v SittingbourneSittingbourne 2-1 East Grinstead Town | Bostik League South East Division |
| 19 | Sat 23 Feb 2019 | 12-1 v Hastings UnitedEast Grinstead Town 2-1 Hastings United | Bostik League South East Division |
| 20 | Tue 26 Feb 2019 | 10-0 v HorshamEast Grinstead Town 0-0 Horsham | Bostik League South East Division |
| 21 | Sat 2 Mar 2019 | 10-2 v Greenwich BoroughGreenwich Borough 2-0 East Grinstead Town | Bostik League South East Division |
| 22 | Sat 9 Mar 2019 | 1 1-1 v Herne BayEast Grinstead Town 1-1 Herne Bay | Bostik League South East Division |
| 23 | Sat 30 Mar 2019 | 15-2 v Hythe TownEast Grinstead Town 5-2 Hythe Town | Bostik League South East Division |
| 24 | Sat 6 Apr 2019 | 11-5 v Phoenix SportsPhoenix Sports 5-1 East Grinstead Town | Bostik League South East Division |
| 25 | Sat 13 Apr 2019 | 1 4-5 v VCD AthleticVCD Athletic 5-4 East Grinstead Town | Bostik League South East Division |
| 26 | Sat 20 Apr 2019 | 14-0 v Whitstable TownEast Grinstead Town 4-0 Whitstable Town | Bostik League South East Division |
| 27 | Mon 22 Apr 2019 | 11-3 v Haywards Heath TownHaywards Heath Town 3-1 East Grinstead Town | Bostik League South East Division |
| 28 | Sat 27 Apr 2019 | 11-2 v Faversham TownEast Grinstead Town 1-2 Faversham Town | Bostik League South East Division |
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