| 1 | Sat 3 Aug 2019 | 1-3 v Sutton UnitedHartlepool United 1-3 Sutton United | Vanarama National League |
| 2 | Sat 10 Aug 2019 | 1-0 v Maidenhead UnitedMaidenhead United 0-1 Hartlepool United | Vanarama National League |
| 3 | Tue 13 Aug 2019 | 2-2 v AFC FyldeHartlepool United 2-2 AFC Fylde | Vanarama National League |
| 4 | Sat 17 Aug 2019 | 2-3 v BromleyHartlepool United 2-3 Bromley | Vanarama National League |
| 5 | Sat 24 Aug 2019 | 0-0 v ChorleyChorley 0-0 Hartlepool United | Vanarama National League |
| 6 | Mon 26 Aug 2019 | 4-2 v WrexhamHartlepool United 4-2 Wrexham | Vanarama National League |
| 7 | Sat 31 Aug 2019 | 2-1 v Torquay UnitedTorquay United 1-2 Hartlepool United | Vanarama National League |
| 8 | Tue 3 Sep 2019 | 1-0 v BarrowBarrow 0-1 Hartlepool United | Vanarama National League |
| 9 | Sat 7 Sep 2019 | 1-1 v WokingHartlepool United 1-1 Woking | Vanarama National League |
| 10 | Sat 14 Sep 2019 | 1-3 v Dagenham & RedbridgeDagenham & Redbridge 3-1 Hartlepool United | Vanarama National League |
| 11 | Sat 21 Sep 2019 | 0-2 v Dover AthleticHartlepool United 0-2 Dover Athletic | Vanarama National League |
| 12 | Tue 24 Sep 2019 | 1-1 v ChesterfieldHartlepool United 1-1 Chesterfield | Vanarama National League |
| 13 | Sat 28 Sep 2019 | 1-1 v EastleighEastleigh 1-1 Hartlepool United | Vanarama National League |
| 14 | Sat 5 Oct 2019 | 2-1 v Yeovil TownHartlepool United 2-1 Yeovil Town | Vanarama National League |
| 15 | Wed 9 Oct 2019 | 1-2 v Stockport CountyStockport County 2-1 Hartlepool United | Vanarama National League |
| 16 | Sat 12 Oct 2019 | 3-0 v Aldershot TownAldershot Town 0-3 Hartlepool United | Vanarama National League |
| 17 | Tue 12 Nov 2019 | 4-1 v Yeovil TownYeovil Town 1-4 Hartlepool United | Emirates FA Cup First Round |
| 18 | Tue 26 Nov 2019 | 5-1 v ChesterfieldChesterfield 1-5 Hartlepool United | Vanarama National League |
| 19 | Sun 1 Dec 2019 | 2-2 v Exeter CityExeter City 2-2 Hartlepool United | Emirates FA Cup Second Round |
| 20 | Sat 7 Dec 2019 | 1-2 v WokingWoking 2-1 Hartlepool United | Vanarama National League |
| 21 | Tue 10 Dec 2019 | 1-0 v Exeter CityHartlepool United 1-0 Exeter City | Emirates FA Cup Second Round Replay |
| 22 | Sat 8 Feb 2020 | 2-0 v Aldershot TownHartlepool United 2-0 Aldershot Town | Vanarama National League |
| 23 | Sat 22 Feb 2020 | 2-0 v Notts CountyHartlepool United 2-0 Notts County | Vanarama National League |
| 24 | Sat 29 Feb 2020 | 1-1 v Boreham WoodBoreham Wood 1-1 Hartlepool United | Vanarama National League |
| 25 | Tue 3 Mar 2020 | 1-0 v Solihull MoorsSolihull Moors 0-1 Hartlepool United | Vanarama National League |
| 26 | Sat 7 Mar 2020 | 0-1 v Ebbsfleet UnitedHartlepool United 0-1 Ebbsfleet United | Vanarama National League |
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