| 1 | Sat 17 Aug 2019 | 90-1 v StamfordGlossop North End 0-1 Stamford | BetVictor Northern South East Division |
| 2 | Tue 20 Aug 2019 | 9 2-0 v Newcastle TownNewcastle Town 0-2 Glossop North End | BetVictor Northern South East Division |
| 3 | Sat 24 Aug 2019 | 91-1 v Eccleshill UnitedEccleshill United 1-1 Glossop North End | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 92-2 v Stocksbridge Park SteelsGlossop North End 2-2 Stocksbridge Park Steels | BetVictor Northern South East Division |
| 5 | Sat 31 Aug 2019 | 160-2 v Belper TownBelper Town 2-0 Glossop North End | BetVictor Northern South East Division |
| 6 | Tue 3 Sep 2019 | 143-1 v Eccleshill UnitedGlossop North End 3-1 Eccleshill United | Emirates FA Cup Preliminary Round |
| 7 | Sat 7 Sep 2019 | 151-3 v Pontefract CollieriesGlossop North End 1-3 Pontefract Collieries | Emirates FA Cup First Qualifying Round |
| 8 | Tue 10 Sep 2019 | 91-1 v Loughborough DynamoGlossop North End 1-1 Loughborough Dynamo | BetVictor Northern South East Division |
| 9 | Sat 14 Sep 2019 | 90-0 v Kidsgrove AthleticKidsgrove Athletic 0-0 Glossop North End | BetVictor Northern South East Division |
| 10 | Sat 21 Sep 2019 | 90-1 v Lincoln UnitedGlossop North End 0-1 Lincoln United | BetVictor Northern South East Division |
| 11 | Tue 24 Sep 2019 | 9 0-1 v Frickley AthleticFrickley Athletic 1-0 Glossop North End | BetVictor Northern South East Division |
| 12 | Tue 1 Oct 2019 | 91-3 v Cleethorpes TownCleethorpes Town 3-1 Glossop North End | BetVictor Northern South East Division |
| 13 | Tue 8 Oct 2019 | 171-4 v Hyde UnitedHyde United 4-1 Glossop North End | Manchester Premier Cup First Round |
| 14 | Sat 23 Nov 2019 | 170-1 v Market Drayton TownGlossop North End 0-1 Market Drayton Town | BetVictor Northern South East Division |
| 15 | Sat 11 Jan 2020 | 172-0 v Worksop TownWorksop Town 0-2 Glossop North End | BetVictor Northern South East Division |
| 16 | Sat 18 Jan 2020 | 91-1 v Sutton Coldfield TownSutton Coldfield Town 1-1 Glossop North End | BetVictor Northern South East Division |
| 17 | Tue 21 Jan 2020 | 121-1 v Worksop TownGlossop North End 1-1 Worksop Town | BetVictor Northern South East Division |
| 18 | Sat 25 Jan 2020 | 91-2 v Cleethorpes TownGlossop North End 1-2 Cleethorpes Town | BetVictor Northern South East Division |
| 19 | Sat 1 Feb 2020 | 171-0 v IlkestonIlkeston 0-1 Glossop North End | BetVictor Northern South East Division |
| 20 | Sat 8 Feb 2020 | 150-1 v SheffieldSheffield 1-0 Glossop North End | BetVictor Northern South East Division |
| 21 | Sat 22 Feb 2020 | 91-1 v Loughborough DynamoLoughborough Dynamo 1-1 Glossop North End | BetVictor Northern South East Division |
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