| 1 | Sat 17 Aug 2019 | 2-2 v Crawley TownScunthorpe United 2-2 Crawley Town | Sky Bet League Two |
| 2 | Tue 20 Aug 2019 | 2-3 v Cambridge UnitedCambridge United 3-2 Scunthorpe United | Sky Bet League Two |
| 3 | Sat 24 Aug 2019 | 0-1 v Macclesfield TownMacclesfield Town 1-0 Scunthorpe United | Sky Bet League Two |
| 4 | Sat 31 Aug 2019 | 0-1 v Carlisle UnitedScunthorpe United 0-1 Carlisle United | Sky Bet League Two |
| 5 | Sat 14 Sep 2019 | 3-0 v MorecambeScunthorpe United 3-0 Morecambe | Sky Bet League Two |
| 6 | Tue 17 Sep 2019 | 2-2 v Oldham AthleticScunthorpe United 2-2 Oldham Athletic | Sky Bet League Two |
| 7 | Sat 21 Sep 2019 | 0-1 v WalsallWalsall 1-0 Scunthorpe United | Sky Bet League Two |
| 8 | Sat 5 Oct 2019 | 2-2 v Plymouth ArgylePlymouth Argyle 2-2 Scunthorpe United | Sky Bet League Two |
| 9 | Sat 26 Oct 2019 | 1-1 v Salford CitySalford City 1-1 Scunthorpe United | Sky Bet League Two |
| 10 | Sat 2 Nov 2019 | 0-0 v StevenageScunthorpe United 0-0 Stevenage | Sky Bet League Two |
| 11 | Sat 9 Nov 2019 | 1-4 v Crawley TownCrawley Town 4-1 Scunthorpe United | Emirates FA Cup First Round |
| 12 | Tue 12 Nov 2019 | 3-0 v SunderlandScunthorpe United 3-0 Sunderland | Leasing.com Trophy Northern Group A |
| 13 | Sat 16 Nov 2019 | 2-0 v Leyton OrientLeyton Orient 0-2 Scunthorpe United | Sky Bet League Two |
| 14 | Sat 23 Nov 2019 | 2-1 v Port ValeScunthorpe United 2-1 Port Vale | Sky Bet League Two |
| 15 | Wed 27 Nov 2019 | 3-1 v BlackpoolBlackpool 1-3 Scunthorpe United | Leasing.com Trophy Second Round |
| 16 | Sat 7 Dec 2019 | 2-0 v Forest Green RoversForest Green Rovers 0-2 Scunthorpe United | Sky Bet League Two |
| 17 | Sat 14 Dec 2019 | 2-2 v Colchester UnitedScunthorpe United 2-2 Colchester United | Sky Bet League Two |
| 18 | Thu 26 Dec 2019 | 0-2 v WalsallScunthorpe United 0-2 Walsall | Sky Bet League Two |
| 19 | Sun 29 Dec 2019 | 1-3 v Crewe AlexandraCrewe Alexandra 3-1 Scunthorpe United | Sky Bet League Two |
| 20 | Wed 1 Jan 2020 | 2-0 v Oldham AthleticOldham Athletic 0-2 Scunthorpe United | Sky Bet League Two |
| 21 | Sat 4 Jan 2020 | 1-3 v Plymouth ArgyleScunthorpe United 1-3 Plymouth Argyle | Sky Bet League Two |
| 22 | Sat 11 Jan 2020 | 1-2 v Newport CountyScunthorpe United 1-2 Newport County | Sky Bet League Two |
| 23 | Sat 18 Jan 2020 | 2-2 v Bradford CityBradford City 2-2 Scunthorpe United | Sky Bet League Two |
| 24 | Tue 21 Jan 2020 | 1-2 v PortsmouthPortsmouth 2-1 Scunthorpe United | Leasing.com Trophy Fourth Round |
| 25 | Sat 1 Feb 2020 | 1-3 v Crawley TownCrawley Town 3-1 Scunthorpe United | Sky Bet League Two |
| 26 | Sat 8 Feb 2020 | 1-0 v Cheltenham TownScunthorpe United 1-0 Cheltenham Town | Sky Bet League Two |
| 27 | Tue 11 Feb 2020 | 0-2 v Cambridge UnitedScunthorpe United 0-2 Cambridge United | Sky Bet League Two |
| 28 | Sat 22 Feb 2020 | 1-0 v Forest Green RoversScunthorpe United 1-0 Forest Green Rovers | Sky Bet League Two |
| 29 | Sat 29 Feb 2020 | 2-2 v Port ValePort Vale 2-2 Scunthorpe United | Sky Bet League Two |
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