Key: Win : Draw : Loss
| Date | Home | Away | Ref | ||
|---|---|---|---|---|---|
| 04/08/2018 | Cheltenham | 0 | 1 | Crawley Town | T Bramall |
| 11/08/2018 | Tranmere | 1 | 0 | Cheltenham | B Toner |
| 18/08/2018 | Cheltenham | 0 | 1 | Carlisle | P Wright |
| 21/08/2018 | Macclesfield | 1 | 1 | Cheltenham | P Marsden |
| 25/08/2018 | Cambridge | 0 | 1 | Cheltenham | M Donohue |
| 01/09/2018 | Cheltenham | 1 | 3 | Colchester | O Yates |
| 08/09/2018 | Northampton | 1 | 3 | Cheltenham | L Collins |
| 15/09/2018 | Cheltenham | 0 | 0 | Crewe | B Huxtable |
| 22/09/2018 | Exeter | 3 | 1 | Cheltenham | M Salisbury |
| 29/09/2018 | Cheltenham | 0 | 2 | Lincoln | D Whitestone |
| 02/10/2018 | Cheltenham | 2 | 2 | Morecambe | N Hair |
| 06/10/2018 | Milton Keynes Dons | 3 | 0 | Cheltenham | T Nield |
| 20/10/2018 | Forest Green | 1 | 1 | Cheltenham | K Johnson |
| 23/10/2018 | Oldham | 2 | 0 | Cheltenham | B Toner |
| 27/10/2018 | Cheltenham | 0 | 2 | Stevenage | M Donohue |
| 03/11/2018 | Cheltenham | 2 | 2 | Mansfield | N Hair |
| 17/11/2018 | Notts County | 0 | 3 | Cheltenham | D Drysdale |
| 24/11/2018 | Cheltenham | 2 | 1 | Newport County | A Young |
| 27/11/2018 | Bury | 4 | 1 | Cheltenham | C Boyeson |
| 08/12/2018 | Cheltenham | 2 | 1 | Grimsby | P Marsden |
| 15/12/2018 | Port Vale | 2 | 2 | Cheltenham | G Salisbury |
| 22/12/2018 | Swindon | 0 | 0 | Cheltenham | L Collins |
| 26/12/2018 | Cheltenham | 3 | 1 | Milton Keynes Dons | D Whitestone |
| 29/12/2018 | Cheltenham | 2 | 2 | Forest Green | R Lewis |
| 01/01/2019 | Yeovil | 1 | 4 | Cheltenham | T Kettle |
| 05/01/2019 | Crawley Town | 1 | 0 | Cheltenham | C Sarginson |
| 12/01/2019 | Cheltenham | 1 | 3 | Tranmere | A Coggins |
| 19/01/2019 | Carlisle | 2 | 0 | Cheltenham | C Boyeson |
| 26/01/2019 | Cheltenham | 3 | 2 | Macclesfield | A Backhouse |
| 05/02/2019 | Cheltenham | 1 | 0 | Yeovil | T Robinson |
| 09/02/2019 | Colchester | 3 | 0 | Cheltenham | C Hicks |
| 16/02/2019 | Grimsby | 1 | 0 | Cheltenham | T Kettle |
| 19/02/2019 | Cheltenham | 2 | 0 | Cambridge | P Marsden |
| 23/02/2019 | Cheltenham | 1 | 0 | Port Vale | P Wright |
| 02/03/2019 | Mansfield | 4 | 2 | Cheltenham | A Young |
| 05/03/2019 | Cheltenham | 1 | 1 | Bury | P Tierney |
| 09/03/2019 | Cheltenham | 4 | 1 | Notts County | T Bramall |
| 15/03/2019 | Newport County | 1 | 0 | Cheltenham | L Swabey |
| 23/03/2019 | Cheltenham | 3 | 1 | Northampton | C Breakspear |
| 30/03/2019 | Crewe | 1 | 3 | Cheltenham | T Kettle |
| 06/04/2019 | Cheltenham | 1 | 1 | Exeter | B Huxtable |
| 13/04/2019 | Lincoln | 1 | 1 | Cheltenham | N Kinseley |
| 19/04/2019 | Cheltenham | 0 | 0 | Oldham | B Toner |
| 22/04/2019 | Morecambe | 4 | 0 | Cheltenham | J Gillett |
| 27/04/2019 | Cheltenham | 3 | 2 | Swindon | T Nield |
| 04/05/2019 | Stevenage | 2 | 0 | Cheltenham | D Whitestone |