| 1 | 17/8/2019 | 100-1 v StamfordGlossop North End 0-1 Stamford | BetVictor Northern South East Division |
| 2 | 20/8/2019 | 10 2-0 v Newcastle TownNewcastle Town 0-2 Glossop North End | BetVictor Northern South East Division |
| 3 | 31/8/2019 | 90-2 v Belper TownBelper Town 2-0 Glossop North End | BetVictor Northern South East Division |
| 4 | 3/9/2019 | 103-1 v Eccleshill UnitedGlossop North End 3-1 Eccleshill United | Emirates FA Cup Preliminary Round |
| 5 | 7/9/2019 | 101-3 v Pontefract CollieriesGlossop North End 1-3 Pontefract Collieries | Emirates FA Cup First Qualifying Round |
| 6 | 10/9/2019 | 101-1 v Loughborough DynamoGlossop North End 1-1 Loughborough Dynamo | BetVictor Northern South East Division |
| 7 | 14/9/2019 | 100-0 v Kidsgrove AthleticKidsgrove Athletic 0-0 Glossop North End | BetVictor Northern South East Division |
| 8 | 21/9/2019 | 160-1 v Lincoln UnitedGlossop North End 0-1 Lincoln United | BetVictor Northern South East Division |
| 9 | 24/9/2019 | 170-1 v Frickley AthleticFrickley Athletic 1-0 Glossop North End | BetVictor Northern South East Division |
| 10 | 1/10/2019 | 111-3 v Cleethorpes TownCleethorpes Town 3-1 Glossop North End | BetVictor Northern South East Division |
| 11 | 5/10/2019 | 176-1 v Spalding UnitedGlossop North End 6-1 Spalding United | BetVictor Northern South East Division |
| 12 | 8/10/2019 | 161-4 v Hyde UnitedHyde United 4-1 Glossop North End | Manchester Premier Cup First Round |
| 13 | 12/10/2019 | 170-2 v Pontefract CollieriesPontefract Collieries 2-0 Glossop North End | Buildbase FA Trophy Preliminary Round |
| 14 | 19/10/2019 | 101-1 v Wisbech TownWisbech Town 1-1 Glossop North End | BetVictor Northern South East Division |
| 15 | 2/11/2019 | 151-1 v Carlton TownGlossop North End 1-1 Carlton Town | BetVictor Northern South East Division |
| 16 | 16/11/2019 | 104-3 v ChasetownGlossop North End 4-3 Chasetown | BetVictor Northern South East Division |
| 17 | 19/11/2019 | 102-2 v FC United of ManchesterFC United of Manchester 2-2 Glossop North End | Integro League Cup First Round |
| 18 | 23/11/2019 | 100-1 v Market Drayton TownGlossop North End 0-1 Market Drayton Town | BetVictor Northern South East Division |
| 19 | 7/12/2019 | 10 3-1 v Lincoln UnitedLincoln United 1-3 Glossop North End | BetVictor Northern South East Division |
