| 1 | Sat 17 Aug 2019 | 4 0-1 v StamfordGlossop North End 0-1 Stamford | BetVictor Northern South East Division |
| 2 | Tue 20 Aug 2019 | 42-0 v Newcastle TownNewcastle Town 0-2 Glossop North End | BetVictor Northern South East Division |
| 3 | Sat 24 Aug 2019 | 41-1 v Eccleshill UnitedEccleshill United 1-1 Glossop North End | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 42-2 v Stocksbridge Park SteelsGlossop North End 2-2 Stocksbridge Park Steels | BetVictor Northern South East Division |
| 5 | Sat 31 Aug 2019 | 40-2 v Belper TownBelper Town 2-0 Glossop North End | BetVictor Northern South East Division |
| 6 | Tue 3 Sep 2019 | 63-1 v Eccleshill UnitedGlossop North End 3-1 Eccleshill United | Emirates FA Cup Preliminary Round |
| 7 | Sat 7 Sep 2019 | 141-3 v Pontefract CollieriesGlossop North End 1-3 Pontefract Collieries | Emirates FA Cup First Qualifying Round |
| 8 | Tue 10 Sep 2019 | 41-1 v Loughborough DynamoGlossop North End 1-1 Loughborough Dynamo | BetVictor Northern South East Division |
| 9 | Tue 1 Oct 2019 | 151-3 v Cleethorpes TownCleethorpes Town 3-1 Glossop North End | BetVictor Northern South East Division |
| 10 | Sat 25 Jan 2020 | 141-2 v Cleethorpes TownGlossop North End 1-2 Cleethorpes Town | BetVictor Northern South East Division |
| 11 | Sat 1 Feb 2020 | 141-0 v IlkestonIlkeston 0-1 Glossop North End | BetVictor Northern South East Division |
| 12 | Sat 8 Feb 2020 | 140-1 v SheffieldSheffield 1-0 Glossop North End | BetVictor Northern South East Division |
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