| Northern Ireland Premier | 2019/10/04 18:45 | Glentoran v Cliftonville | W | 0-1 |
| Northern Ireland Premier | 2019/05/11 16:30 | Cliftonville v Glentoran | W | 2-0 |
| Northern Ireland Premier | 2019/03/30 15:00 | Cliftonville v Glentoran | W | 2-1 |
| Northern Ireland Premier | 2018/11/03 15:00 | Cliftonville v Glentoran | W | 1-0 |
| Northern Ireland Premier | 2018/08/04 14:00 | Glentoran v Cliftonville | W | 1-2 |
| Northern Ireland Premier | 2018/05/12 14:00 | Cliftonville v Glentoran | W | 3-2 |
| Northern Ireland Premier | 2018/02/24 15:00 | Glentoran v Cliftonville | L | 1-0 |
| Northern Ireland Premier | 2017/12/16 15:00 | Cliftonville v Glentoran | W | 1-0 |
| Northern Ireland Premier | 2019/10/19 14:00 | Institute v Cliftonville | W | 0-3 |
| Northern Ireland Premier | 2019/10/12 14:00 | Cliftonville v Larne FC | W | 1-0 |
| Northern Ireland League Cup | 2019/10/08 18:45 | Cliftonville v Bangor FC | W | 3-2 |
| Northern Ireland Premier | 2019/10/04 18:45 | Glentoran v Cliftonville | W | 0-1 |
| Northern Ireland Premier | 2019/09/28 14:00 | Ballymena Utd v Cliftonville | L | 2-1 |
| Club Friendly List | 2019/09/22 13:00 | Crewe United v Cliftonville | W | 2-5 |
| Northern Ireland Premier | 2019/09/21 14:00 | Cliftonville v Institute | W | 1-0 |
| Northern Ireland Premier | 2019/09/14 14:00 | Dungannon Swifts v Cliftonville | W | 0-4 |
| Northern Ireland Premier | 2019/10/25 18:45 | Glentoran v Ballymena Utd | W | 3-1 |
| Northern Ireland Premier | 2019/10/18 18:45 | Larne FC v Glentoran | W | 2-3 |
| Northern Ireland County Antrim Shield | 2019/10/15 18:45 | Glentoran v Larne FC | D | 2-2 |
| Northern Ireland Premier | 2019/10/12 14:00 | Glentoran v Carrick Rangers | W | 3-1 |
| Northern Ireland League Cup | 2019/10/08 18:45 | Coleraine v Glentoran | L | 2-1 |
| Northern Ireland Premier | 2019/10/04 18:45 | Glentoran v Cliftonville | L | 0-1 |
| Northern Ireland Premier | 2019/09/28 14:00 | Crusaders v Glentoran | L | 5-2 |
| Northern Ireland Premier | 2019/09/21 14:00 | Glentoran v Warrenpoint Town | W | 2-1 |