| 1 | Sat 17 Aug 2019 | 5 0-1 v StamfordGlossop North End 0-1 Stamford | BetVictor Northern South East Division |
| 2 | Tue 20 Aug 2019 | 52-0 v Newcastle TownNewcastle Town 0-2 Glossop North End | BetVictor Northern South East Division |
| 3 | Sat 24 Aug 2019 | 51-1 v Eccleshill UnitedEccleshill United 1-1 Glossop North End | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 5 2-2 v Stocksbridge Park SteelsGlossop North End 2-2 Stocksbridge Park Steels | BetVictor Northern South East Division |
| 5 | Sat 7 Sep 2019 | 51-3 v Pontefract CollieriesGlossop North End 1-3 Pontefract Collieries | Emirates FA Cup First Qualifying Round |
| 6 | Tue 24 Sep 2019 | 50-1 v Frickley AthleticFrickley Athletic 1-0 Glossop North End | BetVictor Northern South East Division |
| 7 | Tue 1 Oct 2019 | 51-3 v Cleethorpes TownCleethorpes Town 3-1 Glossop North End | BetVictor Northern South East Division |
| 8 | Sat 5 Oct 2019 | 56-1 v Spalding UnitedGlossop North End 6-1 Spalding United | BetVictor Northern South East Division |
| 9 | Sat 12 Oct 2019 | 120-2 v Pontefract CollieriesPontefract Collieries 2-0 Glossop North End | Buildbase FA Trophy Preliminary Round |
| 10 | Sat 19 Oct 2019 | 61-1 v Wisbech TownWisbech Town 1-1 Glossop North End | BetVictor Northern South East Division |
| 11 | Sat 2 Nov 2019 | 51-1 v Carlton TownGlossop North End 1-1 Carlton Town | BetVictor Northern South East Division |
| 12 | Sat 16 Nov 2019 | 54-3 v ChasetownGlossop North End 4-3 Chasetown | BetVictor Northern South East Division |
| 13 | Tue 19 Nov 2019 | 52-2 v FC United of ManchesterFC United of Manchester 2-2 Glossop North End | Integro League Cup First Round |
| 14 | Sat 23 Nov 2019 | 50-1 v Market Drayton TownGlossop North End 0-1 Market Drayton Town | BetVictor Northern South East Division |
| 15 | Sat 7 Dec 2019 | 5 3-1 v Lincoln UnitedLincoln United 1-3 Glossop North End | BetVictor Northern South East Division |
| 16 | Sat 14 Dec 2019 | 53-2 v IlkestonGlossop North End 3-2 Ilkeston | BetVictor Northern South East Division |
| 17 | Sat 21 Dec 2019 | 51-5 v StamfordStamford 5-1 Glossop North End | BetVictor Northern South East Division |
| 18 | Thu 26 Dec 2019 | 50-3 v Leek TownGlossop North End 0-3 Leek Town | BetVictor Northern South East Division |
| 19 | Sat 11 Jan 2020 | 52-0 v Worksop TownWorksop Town 0-2 Glossop North End | BetVictor Northern South East Division |
| 20 | Sat 18 Jan 2020 | 5 1-1 v Sutton Coldfield TownSutton Coldfield Town 1-1 Glossop North End | BetVictor Northern South East Division |
| 21 | Tue 21 Jan 2020 | 51-1 v Worksop TownGlossop North End 1-1 Worksop Town | BetVictor Northern South East Division |
| 22 | Sat 25 Jan 2020 | 51-2 v Cleethorpes TownGlossop North End 1-2 Cleethorpes Town | BetVictor Northern South East Division |
| 23 | Sat 1 Feb 2020 | 51-0 v IlkestonIlkeston 0-1 Glossop North End | BetVictor Northern South East Division |
| 24 | Sat 8 Feb 2020 | 50-1 v SheffieldSheffield 1-0 Glossop North End | BetVictor Northern South East Division |
| 25 | Sat 22 Feb 2020 | 5 1-1 v Loughborough DynamoLoughborough Dynamo 1-1 Glossop North End | BetVictor Northern South East Division |
| 26 | Sat 7 Mar 2020 | 50-1 v Sutton Coldfield TownGlossop North End 0-1 Sutton Coldfield Town | BetVictor Northern South East Division |
| 27 | Tue 10 Mar 2020 | 5 1-3 v Frickley AthleticGlossop North End 1-3 Frickley Athletic | BetVictor Northern South East Division |
| 28 | Sat 14 Mar 2020 | 50-4 v Carlton TownCarlton Town 4-0 Glossop North End | BetVictor Northern South East Division |
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