| 1 | 3/8/2019 | 1-3 v Sutton UnitedHartlepool United 1-3 Sutton United | Vanarama National League |
| 2 | 6/8/2019 | 0-2 v FC Halifax TownFC Halifax Town 2-0 Hartlepool United | Vanarama National League |
| 3 | 10/8/2019 | 1-0 v Maidenhead UnitedMaidenhead United 0-1 Hartlepool United | Vanarama National League |
| 4 | 13/8/2019 | 2-2 v AFC FyldeHartlepool United 2-2 AFC Fylde | Vanarama National League |
| 5 | 17/8/2019 | 2-3 v BromleyHartlepool United 2-3 Bromley | Vanarama National League |
| 6 | 24/8/2019 | 0-0 v ChorleyChorley 0-0 Hartlepool United | Vanarama National League |
| 7 | 26/8/2019 | 4-2 v WrexhamHartlepool United 4-2 Wrexham | Vanarama National League |
| 8 | 31/8/2019 | 2-1 v Torquay UnitedTorquay United 1-2 Hartlepool United | Vanarama National League |
| 9 | 3/9/2019 | 1-0 v BarrowBarrow 0-1 Hartlepool United | Vanarama National League |
| 10 | 7/9/2019 | 1-1 v WokingHartlepool United 1-1 Woking | Vanarama National League |
| 11 | 14/9/2019 | 1-3 v Dagenham & RedbridgeDagenham & Redbridge 3-1 Hartlepool United | Vanarama National League |
| 12 | 21/9/2019 | 0-2 v Dover AthleticHartlepool United 0-2 Dover Athletic | Vanarama National League |
| 13 | 24/9/2019 | 1-1 v ChesterfieldHartlepool United 1-1 Chesterfield | Vanarama National League |
| 14 | 28/9/2019 | 1-1 v EastleighEastleigh 1-1 Hartlepool United | Vanarama National League |
| 15 | 5/10/2019 | 2-1 v Yeovil TownHartlepool United 2-1 Yeovil Town | Vanarama National League |
| 16 | 9/10/2019 | 1-2 v Stockport CountyStockport County 2-1 Hartlepool United | Vanarama National League |
| 17 | 12/10/2019 | 3-0 v Aldershot TownAldershot Town 0-3 Hartlepool United | Vanarama National League |
| 18 | 26/10/2019 | 2-0 v BarnetHartlepool United 2-0 Barnet | Vanarama National League |
| 19 | 2/11/2019 | 2-2 v Notts CountyNotts County 2-2 Hartlepool United | Vanarama National League |
| 20 | 5/11/2019 | 0-1 v Solihull MoorsHartlepool United 0-1 Solihull Moors | Vanarama National League |
| 21 | 12/11/2019 | 4-1 v Yeovil TownYeovil Town 1-4 Hartlepool United | Emirates FA Cup First Round |
| 22 | 16/11/2019 | 2-2 v Ebbsfleet UnitedEbbsfleet United 2-2 Hartlepool United | Vanarama National League |
| 23 | 23/11/2019 | 2-2 v Boreham WoodHartlepool United 2-2 Boreham Wood | Vanarama National League |
| 24 | 26/11/2019 | 5-1 v ChesterfieldChesterfield 1-5 Hartlepool United | Vanarama National League |
| 25 | 1/12/2019 | 2-2 v Exeter CityExeter City 2-2 Hartlepool United | Emirates FA Cup Second Round |
| 26 | 7/12/2019 | 1-2 v WokingWoking 2-1 Hartlepool United | Vanarama National League |
| 27 | 10/12/2019 | 1-0 v Exeter CityHartlepool United 1-0 Exeter City | Emirates FA Cup Second Round Replay |
