| 1 | Tue 15 Oct 2019 | 2-1 v BlackpoolCarlisle United 2-1 Blackpool | Leasing.com Trophy Northern Group G |
| 2 | Sat 19 Oct 2019 | 0-2 v Plymouth ArgylePlymouth Argyle 2-0 Carlisle United | Sky Bet League Two |
| 3 | Tue 22 Oct 2019 | 0-2 v Northampton TownCarlisle United 0-2 Northampton Town | Sky Bet League Two |
| 4 | Sat 26 Oct 2019 | 1-1 v Leyton OrientLeyton Orient 1-1 Carlisle United | Sky Bet League Two |
| 5 | Sat 2 Nov 2019 | 2-1 v Macclesfield TownCarlisle United 2-1 Macclesfield Town | Sky Bet League Two |
| 6 | Tue 12 Nov 2019 | 1-3 v MorecambeMorecambe 3-1 Carlisle United | Leasing.com Trophy Northern Group G |
| 7 | Sat 16 Nov 2019 | 1-2 v Port ValePort Vale 2-1 Carlisle United | Sky Bet League Two |
| 8 | Sat 23 Nov 2019 | 0-0 v Cambridge UnitedCarlisle United 0-0 Cambridge United | Sky Bet League Two |
| 9 | Sat 7 Dec 2019 | 1-1 v MorecambeMorecambe 1-1 Carlisle United | Sky Bet League Two |
| 10 | Tue 10 Dec 2019 | 1-0 v Forest Green RoversCarlisle United 1-0 Forest Green Rovers | Emirates FA Cup Second Round |
| 11 | Sat 14 Dec 2019 | 0-0 v Grimsby TownCarlisle United 0-0 Grimsby Town | Sky Bet League Two |
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