| 1 | Sat 24 Aug 2019 | 3-0 v WalsallPlymouth Argyle 3-0 Walsall | Sky Bet League Two |
| 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 | Sat 7 Sep 2019 | 2-2 v Oldham AthleticPlymouth Argyle 2-2 Oldham Athletic | Sky Bet League Two |
| 5 | Sat 14 Sep 2019 | 0-1 v Port ValePort Vale 1-0 Plymouth Argyle | Sky Bet League Two |
| 6 | Tue 17 Sep 2019 | 2-2 v Crawley TownCrawley Town 2-2 Plymouth Argyle | Sky Bet League Two |
| 7 | Sat 5 Oct 2019 | 2-2 v Scunthorpe UnitedPlymouth Argyle 2-2 Scunthorpe United | Sky Bet League Two |
| 8 | Tue 8 Oct 2019 | 3-0 v Swindon TownSwindon Town 0-3 Plymouth Argyle | Leasing.com Trophy Southern Group F |
| 9 | Sat 12 Oct 2019 | 1-1 v Swindon TownSwindon Town 1-1 Plymouth Argyle | Sky Bet League Two |
| 10 | Sat 19 Oct 2019 | 2-0 v Carlisle UnitedPlymouth Argyle 2-0 Carlisle United | Sky Bet League Two |
| 11 | Tue 22 Oct 2019 | 4-0 v Leyton OrientPlymouth Argyle 4-0 Leyton Orient | 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 14 Dec 2019 | 3-0 v MorecambePlymouth Argyle 3-0 Morecambe | Sky Bet League Two |
| 14 | Tue 17 Dec 2019 | 0-1 v Bristol RoversPlymouth Argyle 0-1 Bristol Rovers | Emirates FA Cup Second Round |
| 15 | Thu 26 Dec 2019 | 1-0 v Cheltenham TownCheltenham Town 0-1 Plymouth Argyle | Sky Bet League Two |
| 16 | Sun 29 Dec 2019 | 2-1 v StevenagePlymouth Argyle 2-1 Stevenage | Sky Bet League Two |
| 17 | Wed 1 Jan 2020 | 1-2 v Swindon TownPlymouth Argyle 1-2 Swindon Town | Sky Bet League Two |
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