| 1 | Tue 6 Aug 2019 | 0-2 v FC Halifax TownFC Halifax Town 2-0 Hartlepool United | Vanarama National League |
| 2 | Sat 10 Aug 2019 | 1-0 v Maidenhead UnitedMaidenhead United 0-1 Hartlepool United | Vanarama National League |
| 3 | Sat 17 Aug 2019 | 2-3 v BromleyHartlepool United 2-3 Bromley | Vanarama National League |
| 4 | Mon 26 Aug 2019 | 4-2 v WrexhamHartlepool United 4-2 Wrexham | Vanarama National League |
| 5 | Sat 31 Aug 2019 | 2-1 v Torquay UnitedTorquay United 1-2 Hartlepool United | Vanarama National League |
| 6 | Tue 3 Sep 2019 | 1-0 v BarrowBarrow 0-1 Hartlepool United | Vanarama National League |
| 7 | Sat 7 Sep 2019 | 1-1 v WokingHartlepool United 1-1 Woking | Vanarama National League |
| 8 | Sat 14 Sep 2019 | 1-3 v Dagenham & RedbridgeDagenham & Redbridge 3-1 Hartlepool United | Vanarama National League |
| 9 | Sat 21 Sep 2019 | 0-2 v Dover AthleticHartlepool United 0-2 Dover Athletic | Vanarama National League |
| 10 | Tue 24 Sep 2019 | 1-1 v ChesterfieldHartlepool United 1-1 Chesterfield | Vanarama National League |
| 11 | Sat 28 Sep 2019 | 1-1 v EastleighEastleigh 1-1 Hartlepool United | Vanarama National League |
| 12 | Sat 5 Oct 2019 | 2-1 v Yeovil TownHartlepool United 2-1 Yeovil Town | Vanarama National League |
| 13 | Wed 9 Oct 2019 | 1-2 v Stockport CountyStockport County 2-1 Hartlepool United | Vanarama National League |
| 14 | Sat 12 Oct 2019 | 3-0 v Aldershot TownAldershot Town 0-3 Hartlepool United | Vanarama National League |
| 15 | Sat 26 Oct 2019 | 2-0 v BarnetHartlepool United 2-0 Barnet | Vanarama National League |
| 16 | Sat 2 Nov 2019 | 2-2 v Notts CountyNotts County 2-2 Hartlepool United | Vanarama National League |
| 17 | Tue 5 Nov 2019 | 0-1 v Solihull MoorsHartlepool United 0-1 Solihull Moors | Vanarama National League |
| 18 | Tue 12 Nov 2019 | 4-1 v Yeovil TownYeovil Town 1-4 Hartlepool United | Emirates FA Cup First Round |
| 19 | Sat 16 Nov 2019 | 2-2 v Ebbsfleet UnitedEbbsfleet United 2-2 Hartlepool United | Vanarama National League |
| 20 | Sat 23 Nov 2019 | 2-2 v Boreham WoodHartlepool United 2-2 Boreham Wood | Vanarama National League |
| 21 | Tue 26 Nov 2019 | 5-1 v ChesterfieldChesterfield 1-5 Hartlepool United | Vanarama National League |
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