| 1 | Sat 1 Aug | 10-1 v Thornbury TownThornbury Town 1-0 Highworth Town | Hellenic League Premier Division |
| 2 | Tue 4 Aug | 11-4 v Malmesbury VictoriaMalmesbury Victoria 4-1 Highworth Town | Hellenic League Premier Division |
| 3 | Sat 8 Aug | 11-4 v Milton Keynes IrishHighworth Town 1-4 Milton Keynes Irish | Emirates FA Cup Extra Preliminary Round |
| 4 | Sat 15 Aug | 11-0 v Bradford TownHighworth Town 1-0 Bradford Town | FA Vase First Qualifying Round |
| 5 | Tue 18 Aug | 12-4 v Devizes TownDevizes Town 4-2 Highworth Town | Hellenic League Premier Division |
| 6 | Sat 22 Aug | 11-1 v Stourport SwiftsStourport Swifts 1-1 Highworth Town | Hellenic League Premier Division |
| 7 | Sat 29 Aug | 11-1 v Droitwich SpaDroitwich Spa 1-1 Highworth Town | Hellenic League Premier Division |
| 8 | Sat 5 Sep | 16-0 v WestfieldsWestfields 0-6 Highworth Town | Hellenic League Premier Division |
| 9 | Sat 12 Sep | 10-0 v Calne TownCalne Town 0-0 Highworth Town | FA Vase Second Qualifying Round |
| 10 | Sat 19 Sep | 14-1 v Fairford TownFairford Town 1-4 Highworth Town | Hellenic League Premier Division |
| 11 | Tue 22 Sep | 12-1 v Corsham TownCorsham Town 1-2 Highworth Town | Hellenic League Premier Division |
| 12 | Sat 26 Sep | 11-0 v CribbsHighworth Town 1-0 Cribbs | Hellenic League Premier Division |
| 13 | Tue 29 Sep | 11-4 v LonglevensHighworth Town 1-4 Longlevens | Hellenic League Premier Division |
| 14 | Sat 3 Oct | 11-0 v HallenHallen 0-1 Highworth Town | Hellenic League Premier Division |
| 15 | Sat 10 Oct | 13-0 v Hamworthy UnitedHighworth Town 3-0 Hamworthy United | FA Vase First Round |
| 16 | Tue 13 Oct | 12-1 v Cirencester TownHighworth Town 2-1 Cirencester Town | Hellenic League Premier Division |
| 17 | Sat 17 Oct | 11-1 v Hereford PegasusHereford Pegasus 1-1 Highworth Town | Hellenic League Premier Division |
| 18 | Tue 20 Oct | 13-0 v Royal Wootton BassettHighworth Town 3-0 Royal Wootton Bassett | Hellenic League Premier Division |
| 19 | Sat 24 Oct | 14-1 v Bradford TownHighworth Town 4-1 Bradford Town | Hellenic League Premier Division |
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