| 31/07/2018 | Gillingham | 1 | 2 | Tottenham | Lost |
| 07/08/2018 | Liverpool | 0 | 0 | Gillingham | Drawn |
| 14/08/2018 | Gillingham | West Ham | |||
| 21/08/2018 | Southampton | Gillingham | |||
| 28/08/2018 | Gillingham | Man Utd | |||
| 04/09/2018 | Man City | Gillingham | |||
| 11/09/2018 | Gillingham | Arsenal | |||
| 18/09/2018 | Wigan | Gillingham | |||
| 25/09/2018 | Gillingham | Walsall | |||
| 02/10/2018 | Tottenham | Gillingham | |||
| 09/10/2018 | Gillingham | Liverpool | |||
| 16/10/2018 | West Ham | Gillingham | |||
| 23/10/2018 | Gillingham | Southampton | |||
| 30/10/2018 | Man Utd | Gillingham | |||
| 06/11/2018 | Gillingham | Man City | |||
| 13/11/2018 | Arsenal | Gillingham | |||
| 20/11/2018 | Gillingham | Wigan | |||
| 27/11/2018 | Walsall | Gillingham |