| 1 | 3/8/2019 | 2-1 v Crawley TownCarlisle United 2-1 Crawley Town | Sky Bet League Two |
| 2 | 10/8/2019 | 2-3 v Swindon TownSwindon Town 3-2 Carlisle United | Sky Bet League Two |
| 3 | 13/8/2019 | 3-0 v BarnsleyBarnsley 0-3 Carlisle United | Carabao Cup First Round |
| 4 | 17/8/2019 | 0-2 v Mansfield TownCarlisle United 0-2 Mansfield Town | Sky Bet League Two |
| 5 | 20/8/2019 | 0-2 v Cheltenham TownCheltenham Town 2-0 Carlisle United | Sky Bet League Two |
| 6 | 24/8/2019 | 2-2 v Salford CityCarlisle United 2-2 Salford City | Sky Bet League Two |
| 7 | 27/8/2019 | 1-2 v RochdaleRochdale 2-1 Carlisle United | Carabao Cup Second Round |
| 8 | 31/8/2019 | 1-0 v Scunthorpe UnitedScunthorpe United 0-1 Carlisle United | Sky Bet League Two |
| 9 | 7/9/2019 | 1-3 v Exeter CityCarlisle United 1-3 Exeter City | Sky Bet League Two |
| 10 | 15/10/2019 | 2-1 v BlackpoolCarlisle United 2-1 Blackpool | Checkatrade Trophy Northern Group G |
| 11 | 22/10/2019 | 0-2 v Northampton TownCarlisle United 0-2 Northampton Town | Sky Bet League Two |
| 12 | 26/10/2019 | 1-1 v Leyton OrientLeyton Orient 1-1 Carlisle United | Sky Bet League Two |
| 13 | 2/11/2019 | 2-1 v Macclesfield TownCarlisle United 2-1 Macclesfield Town | Sky Bet League Two |
| 14 | 12/11/2019 | 1-3 v MorecambeMorecambe 3-1 Carlisle United | Checkatrade Trophy Northern Group G |
| 15 | 16/11/2019 | 1-2 v Port ValePort Vale 2-1 Carlisle United | Sky Bet League Two |
| 16 | 23/11/2019 | 0-0 v Cambridge UnitedCarlisle United 0-0 Cambridge United | Sky Bet League Two |
| 17 | 30/11/2019 | 2-2 v Forest Green RoversForest Green Rovers 2-2 Carlisle United | Emirates FA Cup Second Round |
| 18 | 10/12/2019 | 1-0 v Forest Green RoversCarlisle United 1-0 Forest Green Rovers | Emirates FA Cup Second Round |
