| 1 | Tue 6 Aug 2019 | 1-1 v Notts CountyNotts County 1-1 Stockport County | Vanarama National League |
| 2 | Sat 10 Aug 2019 | 1-1 v Yeovil TownYeovil Town 1-1 Stockport County | Vanarama National League |
| 3 | Tue 13 Aug 2019 | 3-2 v BarrowStockport County 3-2 Barrow | Vanarama National League |
| 4 | Sat 17 Aug 2019 | 2-0 v EastleighStockport County 2-0 Eastleigh | Vanarama National League |
| 5 | Sat 24 Aug 2019 | 1-2 v Harrogate TownHarrogate Town 2-1 Stockport County | Vanarama National League |
| 6 | Mon 26 Aug 2019 | 2-0 v ChesterfieldStockport County 2-0 Chesterfield | Vanarama National League |
| 7 | Sat 31 Aug 2019 | 2-1 v WrexhamWrexham 1-2 Stockport County | Vanarama National League |
| 8 | Tue 3 Sep 2019 | 2-1 v AFC FyldeStockport County 2-1 AFC Fylde | Vanarama National League |
| 9 | Sat 7 Sep 2019 | 0-3 v ChorleyChorley 3-0 Stockport County | Vanarama National League |
| 10 | Sat 14 Sep 2019 | 1-2 v Aldershot TownStockport County 1-2 Aldershot Town | Vanarama National League |
| 11 | Sat 21 Sep 2019 | 0-4 v Boreham WoodBoreham Wood 4-0 Stockport County | Vanarama National League |
| 12 | Sat 28 Sep 2019 | 0-4 v Torquay UnitedStockport County 0-4 Torquay United | Vanarama National League |
| 13 | Sat 5 Oct 2019 | 0-0 v Sutton UnitedSutton United 0-0 Stockport County | Vanarama National League |
| 14 | Tue 29 Oct 2019 | 2-2 v BromleyBromley 2-2 Stockport County | Vanarama National League |
| 15 | Sat 2 Nov 2019 | 1-3 v WokingStockport County 1-3 Woking | Vanarama National League |
| 16 | Sat 9 Nov 2019 | 1-0 v Dagenham & RedbridgeStockport County 1-0 Dagenham & Redbridge | Vanarama National League |
| 17 | Sat 16 Nov 2019 | 2-1 v BarnetBarnet 1-2 Stockport County | Vanarama National League |
| 18 | Sat 23 Nov 2019 | 1-1 v Ebbsfleet UnitedStockport County 1-1 Ebbsfleet United | Vanarama National League |
| 19 | Tue 26 Nov 2019 | 1-4 v Solihull MoorsStockport County 1-4 Solihull Moors | Vanarama National League |
| 20 | Sat 30 Nov 2019 | 5-1 v Torquay UnitedTorquay United 1-5 Stockport County | Vanarama National League |
| 21 | Sat 7 Dec 2019 | 4-2 v ChorleyStockport County 4-2 Chorley | Vanarama National League |
| 22 | Sat 21 Dec 2019 | 1-2 v Aldershot TownAldershot Town 2-1 Stockport County | Vanarama National League |
| 23 | Thu 26 Dec 2019 | 5-1 v FC Halifax TownStockport County 5-1 FC Halifax Town | Vanarama National League |
| 24 | Sat 28 Dec 2019 | 2-1 v AFC FyldeAFC Fylde 1-2 Stockport County | Vanarama National League |
| 25 | Wed 1 Jan 2020 | 0-0 v FC Halifax TownFC Halifax Town 0-0 Stockport County | Vanarama National League |
| 26 | Sat 4 Jan 2020 | 1-3 v Boreham WoodStockport County 1-3 Boreham Wood | Vanarama National League |
| 27 | Sat 15 Feb 2020 | 1-0 v BromleyStockport County 1-0 Bromley | Vanarama National League |
| 28 | Sat 22 Feb 2020 | 1-1 v WokingWoking 1-1 Stockport County | Vanarama National League |
| 29 | Sat 29 Feb 2020 | 1-0 v Ebbsfleet UnitedEbbsfleet United 0-1 Stockport County | Vanarama National League |
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