| 1 | Tue 8 Oct 2019 | 81-4 v Hyde UnitedHyde United 4-1 Glossop North End | Manchester Premier Cup First Round |
| 2 | Sat 12 Oct 2019 | 8 0-2 v Pontefract CollieriesPontefract Collieries 2-0 Glossop North End | Buildbase FA Trophy Preliminary Round |
| 3 | Tue 19 Nov 2019 | 152-2 v FC United of ManchesterFC United of Manchester 2-2 Glossop North End | Integro League Cup First Round |
| 4 | Sat 18 Jan 2020 | 141-1 v Sutton Coldfield TownSutton Coldfield Town 1-1 Glossop North End | BetVictor Northern South East Division |
| 5 | Tue 21 Jan 2020 | 161-1 v Worksop TownGlossop North End 1-1 Worksop Town | BetVictor Northern South East Division |
| 6 | Sat 1 Feb 2020 | 61-0 v IlkestonIlkeston 0-1 Glossop North End | BetVictor Northern South East Division |
| 7 | Sat 8 Feb 2020 | 70-1 v SheffieldSheffield 1-0 Glossop North End | BetVictor Northern South East Division |
| 8 | Sat 22 Feb 2020 | 121-1 v Loughborough DynamoLoughborough Dynamo 1-1 Glossop North End | BetVictor Northern South East Division |
| 9 | Sat 7 Mar 2020 | 150-1 v Sutton Coldfield TownGlossop North End 0-1 Sutton Coldfield Town | BetVictor Northern South East Division |
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