| 1 | Sat 3 Aug 2019 | 1-3 v Sutton UnitedHartlepool United 1-3 Sutton United | Vanarama National League |
| 2 | Tue 6 Aug 2019 | 0-2 v FC Halifax TownFC Halifax Town 2-0 Hartlepool United | Vanarama National League |
| 3 | Sat 10 Aug 2019 | 1-0 v Maidenhead UnitedMaidenhead United 0-1 Hartlepool United | Vanarama National League |
| 4 | Sat 21 Sep 2019 | 0-2 v Dover AthleticHartlepool United 0-2 Dover Athletic | Vanarama National League |
| 5 | Tue 24 Sep 2019 | 1-1 v ChesterfieldHartlepool United 1-1 Chesterfield | Vanarama National League |
| 6 | Sat 28 Sep 2019 | 1-1 v EastleighEastleigh 1-1 Hartlepool United | Vanarama National League |
| 7 | Sat 12 Oct 2019 | 3-0 v Aldershot TownAldershot Town 0-3 Hartlepool United | Vanarama National League |
| 8 | Sat 26 Oct 2019 | 2-0 v BarnetHartlepool United 2-0 Barnet | Vanarama National League |
| 9 | Sat 2 Nov 2019 | 2-2 v Notts CountyNotts County 2-2 Hartlepool United | Vanarama National League |
| 10 | Tue 5 Nov 2019 | 0-1 v Solihull MoorsHartlepool United 0-1 Solihull Moors | Vanarama National League |
| 11 | Tue 12 Nov 2019 | 4-1 v Yeovil TownYeovil Town 1-4 Hartlepool United | Emirates FA Cup First Round |
| 12 | Sat 16 Nov 2019 | 2-2 v Ebbsfleet UnitedEbbsfleet United 2-2 Hartlepool United | Vanarama National League |
| 13 | Sat 23 Nov 2019 | 2-2 v Boreham WoodHartlepool United 2-2 Boreham Wood | Vanarama National League |
| 14 | Sun 1 Dec 2019 | 2-2 v Exeter CityExeter City 2-2 Hartlepool United | Emirates FA Cup Second Round |
| 15 | Tue 10 Dec 2019 | 1-0 v Exeter CityHartlepool United 1-0 Exeter City | Emirates FA Cup Second Round Replay |
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