| 1 | Sat 3 Aug 2019 | 2-1 v Crawley TownCarlisle United 2-1 Crawley Town | Sky Bet League Two |
| 2 | Tue 13 Aug 2019 | 3-0 v BarnsleyBarnsley 0-3 Carlisle United | Carabao Cup First Round |
| 3 | Sat 17 Aug 2019 | 0-2 v Mansfield TownCarlisle United 0-2 Mansfield Town | Sky Bet League Two |
| 4 | Tue 20 Aug 2019 | 0-2 v Cheltenham TownCheltenham Town 2-0 Carlisle United | Sky Bet League Two |
| 5 | Sat 24 Aug 2019 | 2-2 v Salford CityCarlisle United 2-2 Salford City | Sky Bet League Two |
| 6 | Tue 27 Aug 2019 | 1-2 v RochdaleRochdale 2-1 Carlisle United | Carabao Cup Second Round |
| 7 | Sat 31 Aug 2019 | 1-0 v Scunthorpe UnitedScunthorpe United 0-1 Carlisle United | Sky Bet League Two |
| 8 | Sat 7 Sep 2019 | 1-3 v Exeter CityCarlisle United 1-3 Exeter City | Sky Bet League Two |
| 9 | Tue 15 Oct 2019 | 2-1 v BlackpoolCarlisle United 2-1 Blackpool | Leasing.com Trophy Northern Group G |
| 10 | Sat 19 Oct 2019 | 0-2 v Plymouth ArgylePlymouth Argyle 2-0 Carlisle United | Sky Bet League Two |
| 11 | Sat 26 Oct 2019 | 1-1 v Leyton OrientLeyton Orient 1-1 Carlisle United | Sky Bet League Two |
| 12 | Sat 2 Nov 2019 | 2-1 v Macclesfield TownCarlisle United 2-1 Macclesfield Town | Sky Bet League Two |
| 13 | Tue 12 Nov 2019 | 1-3 v MorecambeMorecambe 3-1 Carlisle United | Leasing.com Trophy Northern Group G |
| 14 | Sat 16 Nov 2019 | 1-2 v Port ValePort Vale 2-1 Carlisle United | Sky Bet League Two |
| 15 | Sat 23 Nov 2019 | 0-0 v Cambridge UnitedCarlisle United 0-0 Cambridge United | Sky Bet League Two |
| 16 | Sat 30 Nov 2019 | 2-2 v Forest Green RoversForest Green Rovers 2-2 Carlisle United | Emirates FA Cup Second Round |
| 17 | Sun 29 Dec 2019 | 2-1 v WalsallWalsall 1-2 Carlisle United | Sky Bet League Two |
| 18 | Wed 1 Jan 2020 | 1-4 v Crewe AlexandraCrewe Alexandra 4-1 Carlisle United | Sky Bet League Two |
| 19 | Wed 15 Jan 2020 | 3-4 v Cardiff CityCarlisle United 3-4 Cardiff City | Emirates FA Cup Third Round |
| 20 | Tue 11 Feb 2020 | 0-1 v Cheltenham TownCarlisle United 0-1 Cheltenham Town | Sky Bet League Two |
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