| 1 | Sat 6 Aug 2016 | 451-1 v Leyton OrientCheltenham Town 1-1 Leyton Orient | Sky Bet League Two |
| 2 | Tue 9 Aug 2016 | 451-0 v Charlton AthleticCheltenham Town 1-0 Charlton Athletic | EFL Cup First Round |
| 3 | Sat 13 Aug 2016 | 11-1 v Mansfield TownMansfield Town 1-1 Cheltenham Town | Sky Bet League Two |
| 4 | Tue 16 Aug 2016 | 11-1 v Carlisle UnitedCarlisle United 1-1 Cheltenham Town | Sky Bet League Two |
| 5 | Sat 20 Aug 2016 | 10-1 v Doncaster RoversCheltenham Town 0-1 Doncaster Rovers | Sky Bet League Two |
| 6 | Tue 23 Aug 2016 | 10-2 v Newcastle UnitedNewcastle United 2-0 Cheltenham Town | EFL Cup Second Round |
| 7 | Sat 27 Aug 2016 | 12-0 v Crewe AlexandraCheltenham Town 2-0 Crewe Alexandra | Sky Bet League Two |
| 8 | Sat 3 Sep 2016 | 10-1 v Plymouth ArgylePlymouth Argyle 1-0 Cheltenham Town | Sky Bet League Two |
| 9 | Sat 10 Sep 2016 | 12-2 v Newport CountyNewport County 2-2 Cheltenham Town | Sky Bet League Two |
| 10 | Sat 17 Sep 2016 | 12-3 v Notts CountyCheltenham Town 2-3 Notts County | Sky Bet League Two |
| 11 | Sat 24 Sep 2016 | 12-4 v Yeovil TownYeovil Town 4-2 Cheltenham Town | Sky Bet League Two |
| 12 | Tue 27 Sep 2016 | 10-0 v StevenageCheltenham Town 0-0 Stevenage | Sky Bet League Two |
| 13 | Sat 1 Oct 2016 | 11-1 v Luton TownCheltenham Town 1-1 Luton Town | Sky Bet League Two |
| 14 | Sat 8 Oct 2016 | 11-1 v Accrington StanleyAccrington Stanley 1-1 Cheltenham Town | Sky Bet League Two |
| 15 | Sat 15 Oct 2016 | 12-1 v Crawley TownCheltenham Town 2-1 Crawley Town | Sky Bet League Two |
| 16 | Sat 22 Oct 2016 | 11-0 v Grimsby TownGrimsby Town 0-1 Cheltenham Town | Sky Bet League Two |
| 17 | Sat 29 Oct 2016 | 12-2 v BlackpoolCheltenham Town 2-2 Blackpool | Sky Bet League Two |
| 18 | Sat 5 Nov 2016 | 11-1 v Crewe AlexandraCheltenham Town 1-1 Crewe Alexandra | Emirates FA Cup First Round |
| 19 | Sat 12 Nov 2016 | 10-2 v Hartlepool UnitedHartlepool United 2-0 Cheltenham Town | Sky Bet League Two |
| 20 | Tue 15 Nov 2016 | 14-1 v Crewe AlexandraCrewe Alexandra 1-4 Cheltenham Town | Emirates FA Cup First Round |
| 21 | Sat 19 Nov 2016 | 11-1 v PortsmouthCheltenham Town 1-1 Portsmouth | Sky Bet League Two |
| 22 | Tue 22 Nov 2016 | 10-3 v Colchester UnitedCheltenham Town 0-3 Colchester United | Sky Bet League Two |
| 23 | Sat 26 Nov 2016 | 11-3 v Cambridge UnitedCambridge United 3-1 Cheltenham Town | Sky Bet League Two |
| 24 | Sat 3 Dec 2016 | 11-2 v Sutton UnitedSutton United 2-1 Cheltenham Town | Emirates FA Cup Second Round |
| 25 | Sat 10 Dec 2016 | 11-3 v Exeter CityCheltenham Town 1-3 Exeter City | Sky Bet League Two |
| 26 | Sat 17 Dec 2016 | 12-1 v MorecambeMorecambe 1-2 Cheltenham Town | Sky Bet League Two |
| 27 | Mon 26 Dec 2016 | 11-2 v BarnetCheltenham Town 1-2 Barnet | Sky Bet League Two |
| 28 | Fri 30 Dec 2016 | 10-1 v Wycombe WanderersCheltenham Town 0-1 Wycombe Wanderers | Sky Bet League Two |
| 29 | Mon 2 Jan 2017 | 10-2 v Colchester UnitedColchester United 2-0 Cheltenham Town | Sky Bet League Two |
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