| 1 | 17/8/2019 | 160-1 v StamfordGlossop North End 0-1 Stamford | BetVictor Northern South East Division |
| 2 | 20/8/2019 | 162-0 v Newcastle TownNewcastle Town 0-2 Glossop North End | BetVictor Northern South East Division |
| 3 | 24/8/2019 | 171-1 v Eccleshill UnitedEccleshill United 1-1 Glossop North End | Emirates FA Cup Preliminary Round |
| 4 | 31/8/2019 | 150-2 v Belper TownBelper Town 2-0 Glossop North End | BetVictor Northern South East Division |
| 5 | 3/9/2019 | 153-1 v Eccleshill UnitedGlossop North End 3-1 Eccleshill United | Emirates FA Cup Preliminary Round |
| 6 | 7/9/2019 | 161-3 v Pontefract CollieriesGlossop North End 1-3 Pontefract Collieries | Emirates FA Cup First Qualifying Round |
| 7 | 10/9/2019 | 141-1 v Loughborough DynamoGlossop North End 1-1 Loughborough Dynamo | BetVictor Northern South East Division |
| 8 | 14/9/2019 | 80-0 v Kidsgrove AthleticKidsgrove Athletic 0-0 Glossop North End | BetVictor Northern South East Division |
| 9 | 21/9/2019 | 80-1 v Lincoln UnitedGlossop North End 0-1 Lincoln United | BetVictor Northern South East Division |
| 10 | 24/9/2019 | 100-1 v Frickley AthleticFrickley Athletic 1-0 Glossop North End | BetVictor Northern South East Division |
| 11 | 1/10/2019 | 121-3 v Cleethorpes TownCleethorpes Town 3-1 Glossop North End | BetVictor Northern South East Division |
| 12 | 5/10/2019 | 166-1 v Spalding UnitedGlossop North End 6-1 Spalding United | BetVictor Northern South East Division |
| 13 | 8/10/2019 | 101-4 v Hyde UnitedHyde United 4-1 Glossop North End | Manchester Premier Cup First Round |
| 14 | 12/10/2019 | 160-2 v Pontefract CollieriesPontefract Collieries 2-0 Glossop North End | Buildbase FA Trophy Preliminary Round |
| 15 | 19/10/2019 | 151-1 v Wisbech TownWisbech Town 1-1 Glossop North End | BetVictor Northern South East Division |
| 16 | 2/11/2019 | 14 1-1 v Carlton TownGlossop North End 1-1 Carlton Town | BetVictor Northern South East Division |
| 17 | 16/11/2019 | 174-3 v ChasetownGlossop North End 4-3 Chasetown | BetVictor Northern South East Division |
| 18 | 19/11/2019 | 142-2 v FC United of ManchesterFC United of Manchester 2-2 Glossop North End | Integro League Cup First Round |
