| 1 | Tue 3 Sep 2019 | 0-3 v Milton Keynes DonsStevenage 0-3 Milton Keynes Dons | Leasing.com Trophy Southern Group G |
| 2 | Sat 14 Sep 2019 | 2-3 v Carlisle UnitedStevenage 2-3 Carlisle United | Sky Bet League Two |
| 3 | Sat 21 Sep 2019 | 0-0 v Forest Green RoversForest Green Rovers 0-0 Stevenage | Sky Bet League Two |
| 4 | Tue 8 Oct 2019 | 1-0 v Wycombe WanderersWycombe Wanderers 0-1 Stevenage | Leasing.com Trophy Southern Group G |
| 5 | Sat 12 Oct 2019 | 2-1 v Grimsby TownStevenage 2-1 Grimsby Town | Sky Bet League Two |
| 6 | Sat 19 Oct 2019 | 1-1 v Port ValePort Vale 1-1 Stevenage | Sky Bet League Two |
| 7 | Tue 22 Oct 2019 | 0-1 v Swindon TownSwindon Town 1-0 Stevenage | Sky Bet League Two |
| 8 | Sat 26 Oct 2019 | 1-0 v MorecambeStevenage 1-0 Morecambe | Sky Bet League Two |
| 9 | Sat 2 Nov 2019 | 0-0 v Scunthorpe UnitedScunthorpe United 0-0 Stevenage | Sky Bet League Two |
| 10 | Sat 7 Dec 2019 | 0-0 v Crawley TownStevenage 0-0 Crawley Town | Sky Bet League Two |
| 11 | Sat 14 Dec 2019 | 1-1 v Newport CountyNewport County 1-1 Stevenage | Sky Bet League Two |
| 12 | Sat 21 Dec 2019 | 1-5 v Crewe AlexandraStevenage 1-5 Crewe Alexandra | Sky Bet League Two |
| 13 | Thu 26 Dec 2019 | 0-0 v Forest Green RoversStevenage 0-0 Forest Green Rovers | Sky Bet League Two |
| 14 | Sun 29 Dec 2019 | 1-2 v Plymouth ArgylePlymouth Argyle 2-1 Stevenage | Sky Bet League Two |
| 15 | Sat 4 Jan 2020 | 0-0 v Colchester UnitedStevenage 0-0 Colchester United | Sky Bet League Two |
| 16 | Tue 11 Feb 2020 | 1-3 v Bradford CityBradford City 3-1 Stevenage | Sky Bet League Two |
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