| 1 | Sat 31 Aug 2019 | 0-1 v Carlisle UnitedScunthorpe United 0-1 Carlisle United | Sky Bet League Two |
| 2 | Sat 14 Sep 2019 | 3-0 v MorecambeScunthorpe United 3-0 Morecambe | Sky Bet League Two |
| 3 | Tue 17 Sep 2019 | 2-2 v Oldham AthleticScunthorpe United 2-2 Oldham Athletic | Sky Bet League Two |
| 4 | Sat 21 Sep 2019 | 0-1 v WalsallWalsall 1-0 Scunthorpe United | Sky Bet League Two |
| 5 | Sat 28 Sep 2019 | 1-1 v Bradford CityScunthorpe United 1-1 Bradford City | Sky Bet League Two |
| 6 | Sat 5 Oct 2019 | 2-2 v Plymouth ArgylePlymouth Argyle 2-2 Scunthorpe United | Sky Bet League Two |
| 7 | Sat 12 Oct 2019 | 3-0 v Northampton TownScunthorpe United 3-0 Northampton Town | Sky Bet League Two |
| 8 | Sat 19 Oct 2019 | 1-2 v Newport CountyNewport County 2-1 Scunthorpe United | Sky Bet League Two |
| 9 | Tue 22 Oct 2019 | 3-1 v Exeter CityScunthorpe United 3-1 Exeter City | Sky Bet League Two |
| 10 | Sat 26 Oct 2019 | 1-1 v Salford CitySalford City 1-1 Scunthorpe United | Sky Bet League Two |
| 11 | Sat 2 Nov 2019 | 0-0 v StevenageScunthorpe United 0-0 Stevenage | Sky Bet League Two |
| 12 | Sat 9 Nov 2019 | 1-4 v Crawley TownCrawley Town 4-1 Scunthorpe United | Emirates FA Cup First Round |
| 13 | Tue 12 Nov 2019 | 3-0 v SunderlandScunthorpe United 3-0 Sunderland | Leasing.com Trophy Northern Group A |
| 14 | Sat 21 Dec 2019 | 1-0 v Grimsby TownGrimsby Town 0-1 Scunthorpe United | Sky Bet League Two |
| 15 | Thu 26 Dec 2019 | 0-2 v WalsallScunthorpe United 0-2 Walsall | Sky Bet League Two |
| 16 | Sun 29 Dec 2019 | 1-3 v Crewe AlexandraCrewe Alexandra 3-1 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 |
| 21 | Tue 21 Jan 2020 | 1-2 v PortsmouthPortsmouth 2-1 Scunthorpe United | Leasing.com Trophy Fourth Round |
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