| 1 | Sat 1 Sep 2018 | 12-1 v Herne BayHerne Bay 1-2 Greenwich Borough | Bostik League South East Division |
| 2 | Sat 15 Sep 2018 | 14-0 v GuernseyGreenwich Borough 4-0 Guernsey | Bostik League South East Division |
| 3 | Tue 18 Sep 2018 | 11-0 v MoleseyMolesey 0-1 Greenwich Borough | Velocity Trophy First Round |
| 4 | Sat 6 Oct 2018 | 10-2 v Whitstable TownWhitstable Town 2-0 Greenwich Borough | Bostik League South East Division |
| 5 | Sat 13 Oct 2018 | 14-1 v Egham TownGreenwich Borough 4-1 Egham Town | Buildbase FA Trophy Preliminary Round |
| 6 | Sat 20 Oct 2018 | 11-2 v RamsgateGreenwich Borough 1-2 Ramsgate | Bostik League South East Division |
| 7 | Sat 27 Oct 2018 | 14-2 v Mildenhall TownMildenhall Town 2-4 Greenwich Borough | Buildbase FA Trophy First Qualifying Round |
| 8 | Tue 30 Oct 2018 | 10-4 v Hastings UnitedHastings United 4-0 Greenwich Borough | Bostik League South East Division |
| 9 | Sat 3 Nov 2018 | 10-1 v Sevenoaks TownGreenwich Borough 0-1 Sevenoaks Town | Bostik League South East Division |
| 10 | Tue 6 Nov 2018 | 11-4 v Whitstable TownWhitstable Town 4-1 Greenwich Borough | Velocity Trophy Second Round |
| 11 | Sat 10 Nov 2018 | 11-0 v Bishop's StortfordGreenwich Borough 1-0 Bishop's Stortford | Buildbase FA Trophy Second Qualifying Round |
| 12 | Tue 13 Nov 2018 | 10-3 v Ashford UnitedGreenwich Borough 0-3 Ashford United | Bostik League South East Division |
| 13 | Sat 17 Nov 2018 | 14-1 v Faversham TownGreenwich Borough 4-1 Faversham Town | Bostik League South East Division |
| 14 | Tue 27 Nov 2018 | 10-2 v HorshamHorsham 2-0 Greenwich Borough | Bostik League South East Division |
| 15 | Sat 1 Dec 2018 | 11-4 v Haywards Heath TownGreenwich Borough 1-4 Haywards Heath Town | Bostik League South East Division |
| 16 | Sat 8 Dec 2018 | 13-1 v East Grinstead TownEast Grinstead Town 1-3 Greenwich Borough | Bostik League South East Division |
| 17 | Tue 11 Dec 2018 | 12-1 v Hythe TownHythe Town 1-2 Greenwich Borough | Bostik League South East Division |
| 18 | Sat 15 Dec 2018 | 12-2 v Three BridgesGreenwich Borough 2-2 Three Bridges | Bostik League South East Division |
| 19 | Sat 22 Dec 2018 | 11-4 v VCD AthleticVCD Athletic 4-1 Greenwich Borough | Bostik League South East Division |
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