| 1 | Sat 17 Aug 2019 | 60-1 v StamfordGlossop North End 0-1 Stamford | BetVictor Northern South East Division |
| 2 | Tue 20 Aug 2019 | 62-0 v Newcastle TownNewcastle Town 0-2 Glossop North End | BetVictor Northern South East Division |
| 3 | Sat 24 Aug 2019 | 61-1 v Eccleshill UnitedEccleshill United 1-1 Glossop North End | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 6 2-2 v Stocksbridge Park SteelsGlossop North End 2-2 Stocksbridge Park Steels | BetVictor Northern South East Division |
| 5 | Sat 31 Aug 2019 | 60-2 v Belper TownBelper Town 2-0 Glossop North End | BetVictor Northern South East Division |
| 6 | Sat 7 Sep 2019 | 61-3 v Pontefract CollieriesGlossop North End 1-3 Pontefract Collieries | Emirates FA Cup First Qualifying Round |
| 7 | Sat 14 Sep 2019 | 50-0 v Kidsgrove AthleticKidsgrove Athletic 0-0 Glossop North End | BetVictor Northern South East Division |
| 8 | Sat 21 Sep 2019 | 60-1 v Lincoln UnitedGlossop North End 0-1 Lincoln United | BetVictor Northern South East Division |
| 9 | Tue 24 Sep 2019 | 60-1 v Frickley AthleticFrickley Athletic 1-0 Glossop North End | BetVictor Northern South East Division |
| 10 | Tue 1 Oct 2019 | 61-3 v Cleethorpes TownCleethorpes Town 3-1 Glossop North End | BetVictor Northern South East Division |
| 11 | Tue 8 Oct 2019 | 121-4 v Hyde UnitedHyde United 4-1 Glossop North End | Manchester Premier Cup First Round |
| 12 | Sat 12 Oct 2019 | 50-2 v Pontefract CollieriesPontefract Collieries 2-0 Glossop North End | Buildbase FA Trophy Preliminary Round |
| 13 | Sat 19 Oct 2019 | 51-1 v Wisbech TownWisbech Town 1-1 Glossop North End | BetVictor Northern South East Division |
| 14 | Sat 2 Nov 2019 | 61-1 v Carlton TownGlossop North End 1-1 Carlton Town | BetVictor Northern South East Division |
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