| 1 | Sat 31 Aug 2019 | 170-2 v Belper TownBelper Town 2-0 Glossop North End | BetVictor Northern South East Division |
| 2 | Tue 3 Sep 2019 | 123-1 v Eccleshill UnitedGlossop North End 3-1 Eccleshill United | Emirates FA Cup Preliminary Round |
| 3 | Tue 24 Sep 2019 | 150-1 v Frickley AthleticFrickley Athletic 1-0 Glossop North End | BetVictor Northern South East Division |
| 4 | Tue 1 Oct 2019 | 31-3 v Cleethorpes TownCleethorpes Town 3-1 Glossop North End | BetVictor Northern South East Division |
| 5 | Sat 12 Oct 2019 | 150-2 v Pontefract CollieriesPontefract Collieries 2-0 Glossop North End | Buildbase FA Trophy Preliminary Round |
| 6 | Sat 19 Oct 2019 | 111-1 v Wisbech TownWisbech Town 1-1 Glossop North End | BetVictor Northern South East Division |
| 7 | Sat 2 Nov 2019 | 111-1 v Carlton TownGlossop North End 1-1 Carlton Town | BetVictor Northern South East Division |
| 8 | Sat 16 Nov 2019 | 114-3 v ChasetownGlossop North End 4-3 Chasetown | BetVictor Northern South East Division |
| 9 | Tue 19 Nov 2019 | 112-2 v FC United of ManchesterFC United of Manchester 2-2 Glossop North End | Integro League Cup First Round |
| 10 | Sat 23 Nov 2019 | 110-1 v Market Drayton TownGlossop North End 0-1 Market Drayton Town | BetVictor Northern South East Division |
| 11 | Sat 7 Dec 2019 | 113-1 v Lincoln UnitedLincoln United 1-3 Glossop North End | BetVictor Northern South East Division |
| 12 | Sat 14 Dec 2019 | 113-2 v IlkestonGlossop North End 3-2 Ilkeston | BetVictor Northern South East Division |
| 13 | Sat 21 Dec 2019 | 111-5 v StamfordStamford 5-1 Glossop North End | BetVictor Northern South East Division |
| 14 | Wed 1 Jan 2020 | 152-1 v Stocksbridge Park SteelsStocksbridge Park Steels 1-2 Glossop North End | BetVictor Northern South East Division |
| 15 | Sat 4 Jan 2020 | 171-1 v Newcastle TownGlossop North End 1-1 Newcastle Town | BetVictor Northern South East Division |
| 16 | Sat 11 Jan 2020 | 82-0 v Worksop TownWorksop Town 0-2 Glossop North End | BetVictor Northern South East Division |
| 17 | Sat 18 Jan 2020 | 151-1 v Sutton Coldfield TownSutton Coldfield Town 1-1 Glossop North End | BetVictor Northern South East Division |
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