Key: Win : Draw : Loss
| Date | Home | Away | Ref | ||
|---|---|---|---|---|---|
| 04/08/2018 | Accrington | 0 | 2 | Gillingham | A Backhouse |
| 11/08/2018 | Gillingham | 3 | 1 | Burton | L Probert |
| 18/08/2018 | Walsall | 2 | 1 | Gillingham | T Kettle |
| 22/08/2018 | Gillingham | 1 | 4 | Sunderland | A Coggins |
| 25/08/2018 | Gillingham | 1 | 1 | Coventry | M Salisbury |
| 01/09/2018 | Barnsley | 2 | 1 | Gillingham | J Busby |
| 08/09/2018 | Gillingham | 0 | 1 | AFC Wimbledon | N Kinseley |
| 15/09/2018 | Rochdale | 3 | 0 | Gillingham | M Coy |
| 22/09/2018 | Gillingham | 2 | 4 | Peterboro | L Swabey |
| 29/09/2018 | Shrewsbury | 2 | 2 | Gillingham | R Joyce |
| 06/10/2018 | Portsmouth | 0 | 2 | Gillingham | C Sarginson |
| 13/10/2018 | Gillingham | 0 | 2 | Southend | J Busby |
| 20/10/2018 | Doncaster | 3 | 3 | Gillingham | G Salisbury |
| 23/10/2018 | Plymouth | 3 | 1 | Gillingham | D England |
| 27/10/2018 | Gillingham | 4 | 0 | Bradford | L Collins |
| 03/11/2018 | Gillingham | 3 | 0 | Fleetwood Town | C Breakspear |
| 06/11/2018 | Gillingham | 0 | 1 | Blackpool | C Hicks |
| 17/11/2018 | Oxford | 1 | 0 | Gillingham | N Hair |
| 24/11/2018 | Gillingham | 1 | 3 | Luton | K Johnson |
| 27/11/2018 | Bristol Rvs | 1 | 2 | Gillingham | O Yates |
| 08/12/2018 | Scunthorpe | 0 | 2 | Gillingham | G Salisbury |
| 15/12/2018 | Gillingham | 2 | 2 | Wycombe | D Whitestone |
| 22/12/2018 | Charlton | 2 | 0 | Gillingham | C Breakspear |
| 26/12/2018 | Gillingham | 2 | 0 | Portsmouth | N Kinseley |
| 29/12/2018 | Gillingham | 1 | 3 | Doncaster | N Hair |
| 01/01/2019 | Southend | 2 | 0 | Gillingham | K Stroud |
| 12/01/2019 | Burton | 2 | 3 | Gillingham | P Wright |
| 19/01/2019 | Gillingham | 0 | 3 | Walsall | D Drysdale |
| 29/01/2019 | Gillingham | 0 | 0 | Accrington | C Hicks |
| 02/02/2019 | Coventry | 1 | 1 | Gillingham | K Johnson |
| 09/02/2019 | Gillingham | 1 | 4 | Barnsley | T Kettle |
| 16/02/2019 | Gillingham | 1 | 0 | Scunthorpe | L Swabey |
| 19/02/2019 | Sunderland | 4 | 2 | Gillingham | M Donohue |
| 23/02/2019 | Wycombe | 0 | 1 | Gillingham | C Boyeson |
| 02/03/2019 | Fleetwood Town | 1 | 1 | Gillingham | N Hair |
| 09/03/2019 | Gillingham | 1 | 0 | Oxford | O Yates |
| 12/03/2019 | Gillingham | 0 | 1 | Bristol Rvs | C Sarginson |
| 16/03/2019 | Luton | 2 | 2 | Gillingham | A Haines |
| 23/03/2019 | AFC Wimbledon | 2 | 4 | Gillingham | L Collins |
| 30/03/2019 | Gillingham | 1 | 1 | Rochdale | A Young |
| 06/04/2019 | Peterboro | 2 | 0 | Gillingham | R Jones |
| 13/04/2019 | Gillingham | 0 | 2 | Shrewsbury | T Bramall |
| 19/04/2019 | Gillingham | 3 | 1 | Plymouth | A Coggins |
| 22/04/2019 | Bradford | 1 | 1 | Gillingham | E Ilderton |
| 27/04/2019 | Gillingham | 0 | 2 | Charlton | L Swabey |
| 04/05/2019 | Blackpool | 0 | 3 | Gillingham | O Yates |