| 1 | Sat 17 Aug 2019 | 2-3 v BromleyHartlepool United 2-3 Bromley | Vanarama National League |
| 2 | Sat 24 Aug 2019 | 0-0 v ChorleyChorley 0-0 Hartlepool United | Vanarama National League |
| 3 | Tue 24 Sep 2019 | 1-1 v ChesterfieldHartlepool United 1-1 Chesterfield | Vanarama National League |
| 4 | Sat 28 Sep 2019 | 1-1 v EastleighEastleigh 1-1 Hartlepool United | Vanarama National League |
| 5 | Sat 26 Oct 2019 | 2-0 v BarnetHartlepool United 2-0 Barnet | Vanarama National League |
| 6 | Sat 2 Nov 2019 | 2-2 v Notts CountyNotts County 2-2 Hartlepool United | Vanarama National League |
| 7 | Tue 5 Nov 2019 | 0-1 v Solihull MoorsHartlepool United 0-1 Solihull Moors | Vanarama National League |
| 8 | Tue 12 Nov 2019 | 4-1 v Yeovil TownYeovil Town 1-4 Hartlepool United | Emirates FA Cup First Round |
| 9 | Sat 16 Nov 2019 | 2-2 v Ebbsfleet UnitedEbbsfleet United 2-2 Hartlepool United | Vanarama National League |
| 10 | Sat 23 Nov 2019 | 2-2 v Boreham WoodHartlepool United 2-2 Boreham Wood | Vanarama National League |
| 11 | Tue 10 Dec 2019 | 1-0 v Exeter CityHartlepool United 1-0 Exeter City | Emirates FA Cup Second Round Replay |
| 12 | Sat 7 Mar 2020 | 0-1 v Ebbsfleet UnitedHartlepool United 0-1 Ebbsfleet United | Vanarama National League |
| 13 | Sat 14 Mar 2020 | 1-1 v Sutton UnitedSutton United 1-1 Hartlepool United | Vanarama National League |
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