| 1 | Sat 17 Aug 2019 | 170-1 v StamfordGlossop North End 0-1 Stamford | BetVictor Northern South East Division |
| 2 | Tue 20 Aug 2019 | 17 2-0 v Newcastle TownNewcastle Town 0-2 Glossop North End | BetVictor Northern South East Division |
| 3 | Sat 24 Aug 2019 | 111-1 v Eccleshill UnitedEccleshill United 1-1 Glossop North End | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 162-2 v Stocksbridge Park SteelsGlossop North End 2-2 Stocksbridge Park Steels | BetVictor Northern South East Division |
| 5 | Tue 3 Sep 2019 | 113-1 v Eccleshill UnitedGlossop North End 3-1 Eccleshill United | Emirates FA Cup Preliminary Round |
| 6 | Sat 7 Sep 2019 | 111-3 v Pontefract CollieriesGlossop North End 1-3 Pontefract Collieries | Emirates FA Cup First Qualifying Round |
| 7 | Tue 10 Sep 2019 | 111-1 v Loughborough DynamoGlossop North End 1-1 Loughborough Dynamo | BetVictor Northern South East Division |
| 8 | Sat 14 Sep 2019 | 110-0 v Kidsgrove AthleticKidsgrove Athletic 0-0 Glossop North End | BetVictor Northern South East Division |
| 9 | Sat 21 Sep 2019 | 110-1 v Lincoln UnitedGlossop North End 0-1 Lincoln United | BetVictor Northern South East Division |
| 10 | Tue 24 Sep 2019 | 110-1 v Frickley AthleticFrickley Athletic 1-0 Glossop North End | BetVictor Northern South East Division |
| 11 | Tue 1 Oct 2019 | 101-3 v Cleethorpes TownCleethorpes Town 3-1 Glossop North End | BetVictor Northern South East Division |
| 12 | Tue 8 Oct 2019 | 141-4 v Hyde UnitedHyde United 4-1 Glossop North End | Manchester Premier Cup First Round |
| 13 | Sat 23 Nov 2019 | 160-1 v Market Drayton TownGlossop North End 0-1 Market Drayton Town | BetVictor Northern South East Division |
| 14 | Sat 7 Dec 2019 | 163-1 v Lincoln UnitedLincoln United 1-3 Glossop North End | BetVictor Northern South East Division |
| 15 | Sat 14 Dec 2019 | 153-2 v IlkestonGlossop North End 3-2 Ilkeston | BetVictor Northern South East Division |
| 16 | Thu 26 Dec 2019 | 80-3 v Leek TownGlossop North End 0-3 Leek Town | BetVictor Northern South East Division |
| 17 | Wed 1 Jan 2020 | 122-1 v Stocksbridge Park SteelsStocksbridge Park Steels 1-2 Glossop North End | BetVictor Northern South East Division |
| 18 | Sat 4 Jan 2020 | 151-1 v Newcastle TownGlossop North End 1-1 Newcastle Town | BetVictor Northern South East Division |
| 19 | Tue 21 Jan 2020 | 111-1 v Worksop TownGlossop North End 1-1 Worksop Town | BetVictor Northern South East Division |
| 20 | Sat 25 Jan 2020 | 111-2 v Cleethorpes TownGlossop North End 1-2 Cleethorpes Town | BetVictor Northern South East Division |
| 21 | Sat 1 Feb 2020 | 111-0 v IlkestonIlkeston 0-1 Glossop North End | BetVictor Northern South East Division |
| 22 | Sat 8 Feb 2020 | 110-1 v SheffieldSheffield 1-0 Glossop North End | BetVictor Northern South East Division |
| 23 | Sat 14 Mar 2020 | 100-4 v Carlton TownCarlton Town 4-0 Glossop North End | BetVictor Northern South East Division |
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