| 1 | Sat 3 Aug 2019 | 1-0 v Northampton TownNorthampton Town 0-1 Walsall | Sky Bet League Two |
| 2 | Sat 10 Aug 2019 | 1-1 v Forest Green RoversWalsall 1-1 Forest Green Rovers | Sky Bet League Two |
| 3 | Sat 24 Aug 2019 | 0-3 v Plymouth ArgylePlymouth Argyle 3-0 Walsall | Sky Bet League Two |
| 4 | Sat 31 Aug 2019 | 1-3 v Grimsby TownWalsall 1-3 Grimsby Town | Sky Bet League Two |
| 5 | Tue 3 Sep 2019 | 0-0 v Coventry CityCoventry City 0-0 Walsall | Leasing.com Trophy Southern Group D |
| 6 | Sat 7 Sep 2019 | 0-0 v Colchester UnitedColchester United 0-0 Walsall | Sky Bet League Two |
| 7 | Sat 14 Sep 2019 | 0-1 v Bradford CityWalsall 0-1 Bradford City | Sky Bet League Two |
| 8 | Tue 17 Sep 2019 | 1-0 v MorecambeMorecambe 0-1 Walsall | Sky Bet League Two |
| 9 | Sat 21 Sep 2019 | 1-0 v Scunthorpe UnitedWalsall 1-0 Scunthorpe United | Sky Bet League Two |
| 10 | Sat 28 Sep 2019 | 3-2 v Crawley TownCrawley Town 2-3 Walsall | Sky Bet League Two |
| 11 | Sat 5 Oct 2019 | 0-3 v Salford CityWalsall 0-3 Salford City | Sky Bet League Two |
| 12 | Sat 12 Oct 2019 | 1-3 v Leyton OrientLeyton Orient 3-1 Walsall | Sky Bet League Two |
| 13 | Sat 19 Oct 2019 | 1-2 v Cheltenham TownWalsall 1-2 Cheltenham Town | Sky Bet League Two |
| 14 | Tue 12 Nov 2019 | 6-0 v Forest Green RoversWalsall 6-0 Forest Green Rovers | Leasing.com Trophy Southern Group D |
| 15 | Wed 20 Nov 2019 | 1-0 v DarlingtonDarlington 0-1 Walsall | Emirates FA Cup First Round Replay |
| 16 | Sat 8 Feb 2020 | 2-0 v Aldershot TownHartlepool United 2-0 Aldershot Town | Vanarama National League |
| 17 | Sat 22 Feb 2020 | 2-0 v Notts CountyHartlepool United 2-0 Notts County | Vanarama National League |
| 18 | Sat 29 Feb 2020 | 1-1 v Boreham WoodBoreham Wood 1-1 Hartlepool United | Vanarama National League |
| 19 | Tue 3 Mar 2020 | 1-0 v Solihull MoorsSolihull Moors 0-1 Hartlepool United | Vanarama National League |
| 20 | Sat 7 Mar 2020 | 0-1 v Ebbsfleet UnitedHartlepool United 0-1 Ebbsfleet United | Vanarama National League |
| 21 | Sat 14 Mar 2020 | 1-1 v Sutton UnitedSutton United 1-1 Hartlepool United | Vanarama National League |
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