| 1 | Sat 23 Nov 2019 | 0-0 v WalsallWalsall 0-0 Stevenage | Sky Bet League Two |
| 2 | Tue 3 Dec 2019 | 2-1 v Colchester UnitedColchester United 1-2 Stevenage | Leasing.com Trophy Second Round |
| 3 | Sat 7 Dec 2019 | 0-0 v Crawley TownStevenage 0-0 Crawley Town | Sky Bet League Two |
| 4 | Sat 14 Dec 2019 | 1-1 v Newport CountyNewport County 1-1 Stevenage | Sky Bet League Two |
| 5 | Thu 26 Dec 2019 | 0-0 v Forest Green RoversStevenage 0-0 Forest Green Rovers | Sky Bet League Two |
| 6 | Sun 29 Dec 2019 | 1-2 v Plymouth ArgylePlymouth Argyle 2-1 Stevenage | Sky Bet League Two |
| 7 | Wed 1 Jan 2020 | 0-1 v Northampton TownNorthampton Town 1-0 Stevenage | Sky Bet League Two |
| 8 | Sat 4 Jan 2020 | 0-0 v Colchester UnitedStevenage 0-0 Colchester United | Sky Bet League Two |
| 9 | Sat 11 Jan 2020 | 0-1 v Port ValeStevenage 0-1 Port Vale | Sky Bet League Two |
| 10 | Tue 14 Jan 2020 | 0-0 v Oldham AthleticStevenage 0-0 Oldham Athletic | Sky Bet League Two |
| 11 | Sat 1 Feb 2020 | 0-3 v Leyton OrientStevenage 0-3 Leyton Orient | Sky Bet League Two |
| 12 | Sat 8 Feb 2020 | 1-2 v Exeter CityExeter City 2-1 Stevenage | Sky Bet League Two |
| 13 | Tue 11 Feb 2020 | 1-3 v Bradford CityBradford City 3-1 Stevenage | Sky Bet League Two |
| 14 | Sat 15 Feb 2020 | 0-1 v Salford CityStevenage 0-1 Salford City | Sky Bet League Two |
| 15 | Sat 7 Mar 2020 | 1-3 v Crewe AlexandraCrewe Alexandra 3-1 Stevenage | Sky Bet League Two |
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