| 1 | 3/8/2019 | 3-0 v Crewe AlexandraCrewe Alexandra 0-3 Plymouth Argyle | Sky Bet League Two |
| 2 | 10/8/2019 | 1-0 v Colchester UnitedPlymouth Argyle 1-0 Colchester United | Sky Bet League Two |
| 3 | 13/8/2019 | 2-0 v Leyton OrientPlymouth Argyle 2-0 Leyton Orient | Carabao Cup First Round |
| 4 | 17/8/2019 | 0-1 v Newport CountyNewport County 1-0 Plymouth Argyle | Sky Bet League Two |
| 5 | 20/8/2019 | 2-2 v Salford CityPlymouth Argyle 2-2 Salford City | Sky Bet League Two |
| 6 | 24/8/2019 | 3-0 v WalsallPlymouth Argyle 3-0 Walsall | Sky Bet League Two |
| 7 | 27/8/2019 | 2-4 v ReadingPlymouth Argyle 2-4 Reading | Carabao Cup Second Round |
| 8 | 31/8/2019 | 1-3 v Northampton TownNorthampton Town 3-1 Plymouth Argyle | Sky Bet League Two |
| 9 | 3/9/2019 | 1-1 v Bristol RoversPlymouth Argyle 1-1 Bristol Rovers | Checkatrade Trophy Southern Group F |
| 10 | 7/9/2019 | 2-2 v Oldham AthleticPlymouth Argyle 2-2 Oldham Athletic | Sky Bet League Two |
| 11 | 21/9/2019 | 0-2 v Cheltenham TownPlymouth Argyle 0-2 Cheltenham Town | Sky Bet League Two |
| 12 | 28/9/2019 | 1-0 v Mansfield TownMansfield Town 0-1 Plymouth Argyle | Sky Bet League Two |
| 13 | 5/10/2019 | 2-2 v Scunthorpe UnitedPlymouth Argyle 2-2 Scunthorpe United | Sky Bet League Two |
| 14 | 8/10/2019 | 3-0 v Swindon TownSwindon Town 0-3 Plymouth Argyle | Checkatrade Trophy Southern Group F |
| 15 | 12/10/2019 | 1-1 v Swindon TownSwindon Town 1-1 Plymouth Argyle | Sky Bet League Two |
| 16 | 19/10/2019 | 2-0 v Carlisle UnitedPlymouth Argyle 2-0 Carlisle United | Sky Bet League Two |
| 17 | 22/10/2019 | 4-0 v Leyton OrientPlymouth Argyle 4-0 Leyton Orient | Sky Bet League Two |
| 18 | 26/10/2019 | 0-4 v Exeter CityExeter City 4-0 Plymouth Argyle | Sky Bet League Two |
| 19 | 9/11/2019 | 1-0 v Bolton WanderersBolton Wanderers 0-1 Plymouth Argyle | Emirates FA Cup First Round |
| 20 | 16/11/2019 | 1-0 v Forest Green RoversForest Green Rovers 0-1 Plymouth Argyle | Sky Bet League Two |
| 21 | 23/11/2019 | 2-1 v Bradford CityPlymouth Argyle 2-1 Bradford City | Sky Bet League Two |
| 22 | 14/12/2019 | 3-0 v MorecambePlymouth Argyle 3-0 Morecambe | Sky Bet League Two |
