| 1 | Tue 13 Aug 2019 | 2-0 v Leyton OrientPlymouth Argyle 2-0 Leyton Orient | Carabao Cup First Round |
| 2 | Tue 27 Aug 2019 | 2-4 v ReadingPlymouth Argyle 2-4 Reading | Carabao Cup Second Round |
| 3 | Sat 31 Aug 2019 | 1-3 v Northampton TownNorthampton Town 3-1 Plymouth Argyle | Sky Bet League Two |
| 4 | Tue 3 Sep 2019 | 1-1 v Bristol RoversPlymouth Argyle 1-1 Bristol Rovers | Leasing.com Trophy Southern Group F |
| 5 | Sat 7 Sep 2019 | 2-2 v Oldham AthleticPlymouth Argyle 2-2 Oldham Athletic | Sky Bet League Two |
| 6 | Sat 14 Sep 2019 | 0-1 v Port ValePort Vale 1-0 Plymouth Argyle | Sky Bet League Two |
| 7 | Tue 17 Sep 2019 | 2-2 v Crawley TownCrawley Town 2-2 Plymouth Argyle | Sky Bet League Two |
| 8 | Sat 21 Sep 2019 | 0-2 v Cheltenham TownPlymouth Argyle 0-2 Cheltenham Town | Sky Bet League Two |
| 9 | Sat 5 Oct 2019 | 2-2 v Scunthorpe UnitedPlymouth Argyle 2-2 Scunthorpe United | Sky Bet League Two |
| 10 | Tue 8 Oct 2019 | 3-0 v Swindon TownSwindon Town 0-3 Plymouth Argyle | Leasing.com Trophy Southern Group F |
| 11 | Sat 19 Oct 2019 | 2-0 v Carlisle UnitedPlymouth Argyle 2-0 Carlisle United | Sky Bet League Two |
| 12 | Sat 26 Oct 2019 | 0-4 v Exeter CityExeter City 4-0 Plymouth Argyle | Sky Bet League Two |
| 13 | Sat 9 Nov 2019 | 1-0 v Bolton WanderersBolton Wanderers 0-1 Plymouth Argyle | Emirates FA Cup First Round |
| 14 | Sat 16 Nov 2019 | 1-0 v Forest Green RoversForest Green Rovers 0-1 Plymouth Argyle | Sky Bet League Two |
| 15 | Sat 23 Nov 2019 | 2-1 v Bradford CityPlymouth Argyle 2-1 Bradford City | Sky Bet League Two |
| 16 | Sun 1 Dec 2019 | 1-1 v Bristol RoversBristol Rovers 1-1 Plymouth Argyle | Emirates FA Cup Second Round |
| 17 | Sat 7 Dec 2019 | 0-1 v Cambridge UnitedCambridge United 1-0 Plymouth Argyle | Sky Bet League Two |
| 18 | Sat 14 Dec 2019 | 3-0 v MorecambePlymouth Argyle 3-0 Morecambe | Sky Bet League Two |
| 19 | Tue 17 Dec 2019 | 0-1 v Bristol RoversPlymouth Argyle 0-1 Bristol Rovers | Emirates FA Cup Second Round |
| 20 | Thu 26 Dec 2019 | 1-0 v Cheltenham TownCheltenham Town 0-1 Plymouth Argyle | Sky Bet League Two |
| 21 | Sun 29 Dec 2019 | 2-1 v StevenagePlymouth Argyle 2-1 Stevenage | Sky Bet League Two |
| 22 | Wed 1 Jan 2020 | 1-2 v Swindon TownPlymouth Argyle 1-2 Swindon Town | Sky Bet League Two |
| 23 | Sat 18 Jan 2020 | 3-1 v Mansfield TownPlymouth Argyle 3-1 Mansfield Town | Sky Bet League Two |
| 24 | Sat 25 Jan 2020 | 2-1 v StevenageStevenage 1-2 Plymouth Argyle | Sky Bet League Two |
| 25 | Tue 28 Jan 2020 | 2-2 v Crawley TownPlymouth Argyle 2-2 Crawley Town | Sky Bet League Two |
| 26 | Sat 8 Feb 2020 | 0-3 v Colchester UnitedColchester United 3-0 Plymouth Argyle | Sky Bet League Two |
| 27 | Tue 11 Feb 2020 | 3-2 v Salford CitySalford City 2-3 Plymouth Argyle | Sky Bet League Two |
| 28 | Sat 15 Feb 2020 | 2-1 v Crewe AlexandraPlymouth Argyle 2-1 Crewe Alexandra | Sky Bet League Two |
| 29 | Tue 18 Feb 2020 | 1-1 v Macclesfield TownMacclesfield Town 1-1 Plymouth Argyle | Sky Bet League Two |
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