| 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 |
| 20 | 14/12/2019 | 103-2 v IlkestonGlossop North End 3-2 Ilkeston | BetVictor Northern South East Division |
| 21 | 21/12/2019 | 101-5 v StamfordStamford 5-1 Glossop North End | BetVictor Northern South East Division |
| 22 | 26/12/2019 | 100-3 v Leek TownGlossop North End 0-3 Leek Town | BetVictor Northern South East Division |
| 23 | 1/1/2020 | 142-1 v Stocksbridge Park SteelsStocksbridge Park Steels 1-2 Glossop North End | BetVictor Northern South East Division |
| 24 | 4/1/2020 | 161-1 v Newcastle TownGlossop North End 1-1 Newcastle Town | BetVictor Northern South East Division |
| 25 | 11/1/2020 | 10 2-0 v Worksop TownWorksop Town 0-2 Glossop North End | BetVictor Northern South East Division |
| 26 | 18/1/2020 | 101-1 v Sutton Coldfield TownSutton Coldfield Town 1-1 Glossop North End | BetVictor Northern South East Division |
| 27 | 21/1/2020 | 101-1 v Worksop TownGlossop North End 1-1 Worksop Town | BetVictor Northern South East Division |
| 28 | 25/1/2020 | 101-2 v Cleethorpes TownGlossop North End 1-2 Cleethorpes Town | BetVictor Northern South East Division |
| 29 | 1/2/2020 | 101-0 v IlkestonIlkeston 0-1 Glossop North End | BetVictor Northern South East Division |
| 30 | 8/2/2020 | 90-1 v SheffieldSheffield 1-0 Glossop North End | BetVictor Northern South East Division |
| 31 | 22/2/2020 | 101-1 v Loughborough DynamoLoughborough Dynamo 1-1 Glossop North End | BetVictor Northern South East Division |
| 32 | 7/3/2020 | 10 0-1 v Sutton Coldfield TownGlossop North End 0-1 Sutton Coldfield Town | BetVictor Northern South East Division |
| 33 | 10/3/2020 | 101-3 v Frickley AthleticGlossop North End 1-3 Frickley Athletic | BetVictor Northern South East Division |
