| 1 | Sat 3 Aug 2019 | 0-2 v Swindon TownScunthorpe United 0-2 Swindon Town | Sky Bet League Two |
| 2 | Sat 10 Aug 2019 | 1-4 v Cheltenham TownCheltenham Town 4-1 Scunthorpe United | Sky Bet League Two |
| 3 | Tue 13 Aug 2019 | 0-1 v Derby CountyScunthorpe United 0-1 Derby County | Carabao Cup First Round |
| 4 | Sat 17 Aug 2019 | 2-2 v Crawley TownScunthorpe United 2-2 Crawley Town | Sky Bet League Two |
| 5 | Tue 20 Aug 2019 | 2-3 v Cambridge UnitedCambridge United 3-2 Scunthorpe United | Sky Bet League Two |
| 6 | Sat 24 Aug 2019 | 0-1 v Macclesfield TownMacclesfield Town 1-0 Scunthorpe United | Sky Bet League Two |
| 7 | Sat 21 Sep 2019 | 0-1 v WalsallWalsall 1-0 Scunthorpe United | Sky Bet League Two |
| 8 | Sat 28 Sep 2019 | 1-1 v Bradford CityScunthorpe United 1-1 Bradford City | Sky Bet League Two |
| 9 | Sat 5 Oct 2019 | 2-2 v Plymouth ArgylePlymouth Argyle 2-2 Scunthorpe United | Sky Bet League Two |
| 10 | Sat 12 Oct 2019 | 3-0 v Northampton TownScunthorpe United 3-0 Northampton Town | Sky Bet League Two |
| 11 | Sat 16 Nov 2019 | 2-0 v Leyton OrientLeyton Orient 0-2 Scunthorpe United | Sky Bet League Two |
| 12 | Sat 23 Nov 2019 | 2-1 v Port ValeScunthorpe United 2-1 Port Vale | Sky Bet League Two |
| 13 | Wed 27 Nov 2019 | 3-1 v BlackpoolBlackpool 1-3 Scunthorpe United | Leasing.com Trophy Second Round |
| 14 | Sat 7 Dec 2019 | 2-0 v Forest Green RoversForest Green Rovers 0-2 Scunthorpe United | Sky Bet League Two |
| 15 | Sat 14 Dec 2019 | 2-2 v Colchester UnitedScunthorpe United 2-2 Colchester United | Sky Bet League Two |
| 16 | Sat 21 Dec 2019 | 1-0 v Grimsby TownGrimsby Town 0-1 Scunthorpe United | Sky Bet League Two |
| 17 | Wed 1 Jan 2020 | 2-0 v Oldham AthleticOldham Athletic 0-2 Scunthorpe United | Sky Bet League Two |
| 18 | Sat 4 Jan 2020 | 1-3 v Plymouth ArgyleScunthorpe United 1-3 Plymouth Argyle | Sky Bet League Two |
| 19 | Sat 11 Jan 2020 | 1-2 v Newport CountyScunthorpe United 1-2 Newport County | Sky Bet League Two |
| 20 | Sat 18 Jan 2020 | 2-2 v Bradford CityBradford City 2-2 Scunthorpe United | Sky Bet League Two |
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