| 1 | Sat 6 Aug 2016 | 101-1 v Leyton OrientCheltenham Town 1-1 Leyton Orient | Sky Bet League Two |
| 2 | Tue 9 Aug 2016 | 101-0 v Charlton AthleticCheltenham Town 1-0 Charlton Athletic | EFL Cup First Round |
| 3 | Sat 13 Aug 2016 | 101-1 v Mansfield TownMansfield Town 1-1 Cheltenham Town | Sky Bet League Two |
| 4 | Sat 20 Aug 2016 | 100-1 v Doncaster RoversCheltenham Town 0-1 Doncaster Rovers | Sky Bet League Two |
| 5 | Tue 23 Aug 2016 | 100-2 v Newcastle UnitedNewcastle United 2-0 Cheltenham Town | EFL Cup Second Round |
| 6 | Sat 27 Aug 2016 | 102-0 v Crewe AlexandraCheltenham Town 2-0 Crewe Alexandra | Sky Bet League Two |
| 7 | Tue 30 Aug 2016 | 101-2 v BlackpoolBlackpool 2-1 Cheltenham Town | Checkatrade Trophy Northern Group A |
| 8 | Sat 3 Sep 2016 | 100-1 v Plymouth ArgylePlymouth Argyle 1-0 Cheltenham Town | Sky Bet League Two |
| 9 | Tue 27 Sep 2016 | 100-0 v StevenageCheltenham Town 0-0 Stevenage | Sky Bet League Two |
| 10 | Sat 1 Oct 2016 | 101-1 v Luton TownCheltenham Town 1-1 Luton Town | Sky Bet League Two |
| 11 | Sat 15 Oct 2016 | 102-1 v Crawley TownCheltenham Town 2-1 Crawley Town | Sky Bet League Two |
| 12 | Sat 22 Oct 2016 | 101-0 v Grimsby TownGrimsby Town 0-1 Cheltenham Town | Sky Bet League Two |
| 13 | Sat 29 Oct 2016 | 102-2 v BlackpoolCheltenham Town 2-2 Blackpool | Sky Bet League Two |
| 14 | Sat 12 Nov 2016 | 100-2 v Hartlepool UnitedHartlepool United 2-0 Cheltenham Town | Sky Bet League Two |
| 15 | Tue 22 Nov 2016 | 100-3 v Colchester UnitedCheltenham Town 0-3 Colchester United | Sky Bet League Two |
| 16 | Sat 26 Nov 2016 | 101-3 v Cambridge UnitedCambridge United 3-1 Cheltenham Town | Sky Bet League Two |
| 17 | Sat 10 Dec 2016 | 101-3 v Exeter CityCheltenham Town 1-3 Exeter City | Sky Bet League Two |
| 18 | Sat 17 Dec 2016 | 102-1 v MorecambeMorecambe 1-2 Cheltenham Town | Sky Bet League Two |
| 19 | Mon 26 Dec 2016 | 101-2 v BarnetCheltenham Town 1-2 Barnet | Sky Bet League Two |
| 20 | Fri 30 Dec 2016 | 100-1 v Wycombe WanderersCheltenham Town 0-1 Wycombe Wanderers | Sky Bet League Two |
| 21 | Mon 2 Jan 2017 | 100-2 v Colchester UnitedColchester United 2-0 Cheltenham Town | Sky Bet League Two |
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