| 1 | Sat 3 Aug 2019 | 3-0 v Crewe AlexandraCrewe Alexandra 0-3 Plymouth Argyle | Sky Bet League Two |
| 2 | Sat 10 Aug 2019 | 1-0 v Colchester UnitedPlymouth Argyle 1-0 Colchester United | Sky Bet League Two |
| 3 | Tue 13 Aug 2019 | 2-0 v Leyton OrientPlymouth Argyle 2-0 Leyton Orient | Carabao Cup First Round |
| 4 | Sat 17 Aug 2019 | 0-1 v Newport CountyNewport County 1-0 Plymouth Argyle | Sky Bet League Two |
| 5 | Tue 20 Aug 2019 | 2-2 v Salford CityPlymouth Argyle 2-2 Salford City | Sky Bet League Two |
| 6 | Sat 24 Aug 2019 | 3-0 v WalsallPlymouth Argyle 3-0 Walsall | Sky Bet League Two |
| 7 | Tue 27 Aug 2019 | 2-4 v ReadingPlymouth Argyle 2-4 Reading | Carabao Cup Second Round |
| 8 | Tue 3 Sep 2019 | 1-1 v Bristol RoversPlymouth Argyle 1-1 Bristol Rovers | Leasing.com Trophy Southern Group F |
| 9 | Sat 7 Sep 2019 | 2-2 v Oldham AthleticPlymouth Argyle 2-2 Oldham Athletic | Sky Bet League Two |
| 10 | Sat 14 Sep 2019 | 0-1 v Port ValePort Vale 1-0 Plymouth Argyle | Sky Bet League Two |
| 11 | Tue 17 Sep 2019 | 2-2 v Crawley TownCrawley Town 2-2 Plymouth Argyle | Sky Bet League Two |
| 12 | Sat 12 Oct 2019 | 1-1 v Swindon TownSwindon Town 1-1 Plymouth Argyle | Sky Bet League Two |
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