| 1 | Sat 10 Aug 2019 | 0-1 v Exeter CityStevenage 0-1 Exeter City | Sky Bet League Two |
| 2 | Sat 17 Aug 2019 | 0-0 v Leyton OrientLeyton Orient 0-0 Stevenage | Sky Bet League Two |
| 3 | Tue 20 Aug 2019 | 0-1 v Bradford CityStevenage 0-1 Bradford City | Sky Bet League Two |
| 4 | Sat 24 Aug 2019 | 0-0 v Mansfield TownMansfield Town 0-0 Stevenage | Sky Bet League Two |
| 5 | Sat 31 Aug 2019 | 2-2 v Macclesfield TownStevenage 2-2 Macclesfield Town | Sky Bet League Two |
| 6 | Tue 3 Sep 2019 | 0-3 v Milton Keynes DonsStevenage 0-3 Milton Keynes Dons | Leasing.com Trophy Southern Group G |
| 7 | Sat 5 Oct 2019 | 1-3 v Colchester UnitedColchester United 3-1 Stevenage | Sky Bet League Two |
| 8 | Tue 19 Nov 2019 | 0-2 v Peterborough UnitedPeterborough United 2-0 Stevenage | Emirates FA Cup First Round Replay |
| 9 | Tue 3 Dec 2019 | 2-1 v Colchester UnitedColchester United 1-2 Stevenage | Leasing.com Trophy Second Round |
| 10 | Sat 21 Dec 2019 | 1-5 v Crewe AlexandraStevenage 1-5 Crewe Alexandra | Sky Bet League Two |
| 11 | Wed 1 Jan 2020 | 0-1 v Northampton TownNorthampton Town 1-0 Stevenage | Sky Bet League Two |
| 12 | Sat 4 Jan 2020 | 0-0 v Colchester UnitedStevenage 0-0 Colchester United | Sky Bet League Two |
| 13 | Sat 8 Feb 2020 | 1-2 v Exeter CityExeter City 2-1 Stevenage | Sky Bet League Two |
| 14 | Tue 11 Feb 2020 | 1-3 v Bradford CityBradford City 3-1 Stevenage | Sky Bet League Two |
| 15 | Sat 15 Feb 2020 | 0-1 v Salford CityStevenage 0-1 Salford City | Sky Bet League Two |
| 16 | Sat 22 Feb 2020 | 0-2 v Crawley TownCrawley Town 2-0 Stevenage | Sky Bet League Two |
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