1 | Sat 10 Aug 2019 | 4-1 v Scunthorpe UnitedCheltenham Town 4-1 Scunthorpe United | Sky Bet League Two |
2 | Tue 13 Aug 2019 | 0-3 v Bristol RoversBristol Rovers 3-0 Cheltenham Town | Carabao Cup First Round |
3 | Tue 20 Aug 2019 | 2-0 v Carlisle UnitedCheltenham Town 2-0 Carlisle United | Sky Bet League Two |
4 | Sat 24 Aug 2019 | 2-2 v Swindon TownCheltenham Town 2-2 Swindon Town | Sky Bet League Two |
5 | Sat 31 Aug 2019 | 0-1 v Crawley TownCrawley Town 1-0 Cheltenham Town | Sky Bet League Two |
6 | Tue 3 Sep 2019 | 0-1 v Exeter CityExeter City 1-0 Cheltenham Town | Leasing.com Trophy Southern Group E |
7 | Sat 28 Sep 2019 | 1-1 v Crewe AlexandraCheltenham Town 1-1 Crewe Alexandra | Sky Bet League Two |
8 | Sat 5 Oct 2019 | 1-1 v Oldham AthleticOldham Athletic 1-1 Cheltenham Town | Sky Bet League Two |
9 | Tue 12 Nov 2019 | 4-7 v Newport CountyCheltenham Town 4-7 Newport County | Leasing.com Trophy Southern Group E |
10 | Tue 19 Nov 2019 | 1-0 v Swindon TownSwindon Town 0-1 Cheltenham Town | Emirates FA Cup First Round Replay |
11 | Sat 21 Dec 2019 | 1-1 v Port ValePort Vale 1-1 Cheltenham Town | Sky Bet League Two |
12 | Thu 26 Dec 2019 | 0-1 v Plymouth ArgyleCheltenham Town 0-1 Plymouth Argyle | Sky Bet League Two |
13 | Sun 29 Dec 2019 | 1-1 v Northampton TownNorthampton Town 1-1 Cheltenham Town | Sky Bet League Two |
14 | Wed 1 Jan 2020 | 1-1 v Newport CountyNewport County 1-1 Cheltenham Town | Sky Bet League Two |
15 | Sat 4 Jan 2020 | 3-0 v Oldham AthleticCheltenham Town 3-0 Oldham Athletic | Sky Bet League Two |
16 | Sat 11 Jan 2020 | 3-1 v WalsallCheltenham Town 3-1 Walsall | Sky Bet League Two |
17 | Sat 18 Jan 2020 | 0-1 v Crewe AlexandraCrewe Alexandra 1-0 Cheltenham Town | Sky Bet League Two |