| 1 | Sat 10 Aug 2019 | 11-0 v Merthyr TownHarrow Borough 1-0 Merthyr Town | BetVictor Southern Premier South |
| 2 | Sat 17 Aug 2019 | 11-1 v Hartley WintneyHartley Wintney 1-1 Harrow Borough | BetVictor Southern Premier South |
| 3 | Mon 26 Aug 2019 | 12-1 v Walton CasualsWalton Casuals 1-2 Harrow Borough | BetVictor Southern Premier South |
| 4 | Sat 7 Sep 2019 | 15-0 v Binfield TownHarrow Borough 5-0 Binfield Town | Emirates FA Cup First Qualifying Round |
| 5 | Tue 10 Sep 2019 | 12-3 v Beaconsfield TownBeaconsfield Town 3-2 Harrow Borough | CSS League Challenge Cup Preliminary Round |
| 6 | Tue 17 Sep 2019 | 11-2 v Beaconsfield TownHarrow Borough 1-2 Beaconsfield Town | BetVictor Southern Premier South |
| 7 | Sat 21 Sep 2019 | 10-1 v Carshalton AthleticHarrow Borough 0-1 Carshalton Athletic | Emirates FA Cup Second Qualifying Round |
| 8 | Tue 24 Sep 2019 | 13-1 v Blackfield & LangleyHarrow Borough 3-1 Blackfield & Langley | BetVictor Southern Premier South |
| 9 | Sat 28 Sep 2019 | 10-2 v Gosport BoroughHarrow Borough 0-2 Gosport Borough | BetVictor Southern Premier South |
| 10 | Sat 12 Oct 2019 | 11-2 v Truro CityHarrow Borough 1-2 Truro City | BetVictor Southern Premier South |
| 11 | Tue 15 Oct 2019 | 11-1 v Chesham UnitedChesham United 1-1 Harrow Borough | BetVictor Southern Premier South |
| 12 | Sat 19 Oct 2019 | 11-3 v SalisburySalisbury 3-1 Harrow Borough | BetVictor Southern Premier South |
| 13 | Tue 22 Oct 2019 | 11-2 v Metropolitan PoliceHarrow Borough 1-2 Metropolitan Police | BetVictor Southern Premier South |
| 14 | Sat 26 Oct 2019 | 10-2 v AFC SudburyAFC Sudbury 2-0 Harrow Borough | Buildbase FA Trophy First Qualifying Round |
| 15 | Tue 29 Oct 2019 | 11-1 v Weston-super-MareWeston-super-Mare 1-1 Harrow Borough | BetVictor Southern Premier South |
| 16 | Sat 2 Nov 2019 | 12-1 v Dorchester TownDorchester Town 1-2 Harrow Borough | BetVictor Southern Premier South |
| 17 | Sat 9 Nov 2019 | 12-3 v Swindon SupermarineHarrow Borough 2-3 Swindon Supermarine | BetVictor Southern Premier South |
| 18 | Sat 16 Nov 2019 | 11-1 v FarnboroughFarnborough 1-1 Harrow Borough | BetVictor Southern Premier South |
| 19 | Sat 23 Nov 2019 | 10-1 v Wimborne TownHarrow Borough 0-1 Wimborne Town | BetVictor Southern Premier South |
| 20 | Sat 30 Nov 2019 | 11-2 v Yate TownYate Town 2-1 Harrow Borough | BetVictor Southern Premier South |
| 21 | Sat 11 Jan 2020 | 13-2 v Hayes & Yeading UnitedHarrow Borough 3-2 Hayes & Yeading United | BetVictor Southern Premier South |
| 22 | Sat 18 Jan 2020 | 10-2 v Blackfield & LangleyBlackfield & Langley 2-0 Harrow Borough | BetVictor Southern Premier South |
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