| 1 | Sat 17 Aug 2019 | 1-1 v Exeter CityExeter City 1-1 Swindon Town | Sky Bet League Two |
| 2 | Tue 20 Aug 2019 | 0-1 v Northampton TownSwindon Town 0-1 Northampton Town | Sky Bet League Two |
| 3 | Sat 24 Aug 2019 | 2-2 v Cheltenham TownCheltenham Town 2-2 Swindon Town | Sky Bet League Two |
| 4 | Sat 31 Aug 2019 | 3-1 v MorecambeSwindon Town 3-1 Morecambe | Sky Bet League Two |
| 5 | Sat 7 Sep 2019 | 3-1 v Leyton OrientLeyton Orient 1-3 Swindon Town | Sky Bet League Two |
| 6 | Sat 14 Sep 2019 | 3-0 v Macclesfield TownSwindon Town 3-0 Macclesfield Town | Sky Bet League Two |
| 7 | Tue 17 Sep 2019 | 0-3 v Colchester UnitedSwindon Town 0-3 Colchester United | Sky Bet League Two |
| 8 | Sat 21 Sep 2019 | 1-0 v Cambridge UnitedCambridge United 0-1 Swindon Town | Sky Bet League Two |
| 9 | Sat 28 Sep 2019 | 0-2 v Newport CountySwindon Town 0-2 Newport County | Sky Bet League Two |
| 10 | Tue 8 Oct 2019 | 0-3 v Plymouth ArgyleSwindon Town 0-3 Plymouth Argyle | Leasing.com Trophy Southern Group F |
| 11 | Sat 19 Oct 2019 | 1-3 v Crewe AlexandraCrewe Alexandra 3-1 Swindon Town | Sky Bet League Two |
| 12 | Tue 22 Oct 2019 | 1-0 v StevenageSwindon Town 1-0 Stevenage | Sky Bet League Two |
| 13 | Sat 26 Oct 2019 | 4-0 v Crawley TownCrawley Town 0-4 Swindon Town | Sky Bet League Two |
| 14 | Sat 2 Nov 2019 | 2-1 v WalsallSwindon Town 2-1 Walsall | Sky Bet League Two |
| 15 | Sat 16 Nov 2019 | 3-2 v Salford CitySalford City 2-3 Swindon Town | Sky Bet League Two |
| 16 | Sat 23 Nov 2019 | 1-0 v Mansfield TownSwindon Town 1-0 Mansfield Town | Sky Bet League Two |
| 17 | Sat 7 Dec 2019 | 3-0 v Grimsby TownGrimsby Town 0-3 Swindon Town | Sky Bet League Two |
| 18 | Sat 14 Dec 2019 | 2-0 v Oldham AthleticSwindon Town 2-0 Oldham Athletic | Sky Bet League Two |
| 19 | Sat 21 Dec 2019 | 2-2 v Forest Green RoversForest Green Rovers 2-2 Swindon Town | Sky Bet League Two |
| 20 | Thu 26 Dec 2019 | 4-0 v Cambridge UnitedSwindon Town 4-0 Cambridge United | Sky Bet League Two |
| 21 | Sun 29 Dec 2019 | 0-2 v Port ValePort Vale 2-0 Swindon Town | Sky Bet League Two |
| 22 | Wed 1 Jan 2020 | 2-1 v Plymouth ArgylePlymouth Argyle 1-2 Swindon Town | Sky Bet League Two |
| 23 | Sat 1 Feb 2020 | 2-1 v Exeter CitySwindon Town 2-1 Exeter City | Sky Bet League Two |
| 24 | Sat 8 Feb 2020 | 1-1 v Carlisle UnitedCarlisle United 1-1 Swindon Town | Sky Bet League Two |
| 25 | Tue 11 Feb 2020 | 1-0 v Northampton TownNorthampton Town 0-1 Swindon Town | Sky Bet League Two |
| 26 | Sat 22 Feb 2020 | 3-1 v Grimsby TownSwindon Town 3-1 Grimsby Town | Sky Bet League Two |
| 27 | Tue 3 Mar 2020 | 2-0 v Scunthorpe UnitedSwindon Town 2-0 Scunthorpe United | Sky Bet League Two |
| 28 | Sat 7 Mar 2020 | 0-2 v Forest Green RoversSwindon Town 0-2 Forest Green Rovers | Sky Bet League Two |
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