| 1 | Sat 30 Aug 2014 | 261-0 v Hartlepool UnitedCheltenham Town 1-0 Hartlepool United | Sky Bet League Two |
| 2 | Tue 2 Sep 2014 | 262-0 v Oxford UnitedCheltenham Town 2-0 Oxford United | Johnstone's Paint Trophy Southern Area First Round |
| 3 | Sat 6 Sep 2014 | 260-0 v MorecambeMorecambe 0-0 Cheltenham Town | Sky Bet League Two |
| 4 | Sat 13 Sep 2014 | 260-1 v Luton TownLuton Town 1-0 Cheltenham Town | Sky Bet League Two |
| 5 | Tue 16 Sep 2014 | 260-1 v Southend UnitedCheltenham Town 0-1 Southend United | Sky Bet League Two |
| 6 | Sat 20 Sep 2014 | 261-1 v Dagenham & RedbridgeCheltenham Town 1-1 Dagenham & Redbridge | Sky Bet League Two |
| 7 | Sat 27 Sep 2014 | 260-1 v Burton AlbionBurton Albion 1-0 Cheltenham Town | Sky Bet League Two |
| 8 | Sat 4 Oct 2014 | 261-1 v AFC WimbledonCheltenham Town 1-1 AFC Wimbledon | Sky Bet League Two |
| 9 | Wed 8 Oct 2014 | 261-3 v Bristol CityCheltenham Town 1-3 Bristol City | Johnstone's Paint Trophy Southern Area Second Round |
| 10 | Sat 11 Oct 2014 | 261-3 v Shrewsbury TownShrewsbury Town 3-1 Cheltenham Town | Sky Bet League Two |
| 11 | Sat 18 Oct 2014 | 263-2 v Northampton TownCheltenham Town 3-2 Northampton Town | Sky Bet League Two |
| 12 | Tue 21 Oct 2014 | 262-1 v Cambridge UnitedCambridge United 1-2 Cheltenham Town | Sky Bet League Two |
| 13 | Sat 1 Nov 2014 | 260-1 v York CityCheltenham Town 0-1 York City | Sky Bet League Two |
| 14 | Sat 8 Nov 2014 | 265-0 v Swindon TownCheltenham Town 5-0 Swindon Town | FA Cup First Round |
| 15 | Sat 15 Nov 2014 | 261-5 v StevenageStevenage 5-1 Cheltenham Town | Sky Bet League Two |
| 16 | Sat 22 Nov 2014 | 261-4 v Wycombe WanderersCheltenham Town 1-4 Wycombe Wanderers | Sky Bet League Two |
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