[1] Cliftonville 1-0 Glentoran [5] 2021-09-04 14:00
Stadium: Solitude Round: 3
Home Manager: Paddy McLaughlin Away Manager: Michael McDermott
Head to Head
| Northern Ireland Premier | 2021/05/15 14:00 | Glentoran v Cliftonville | W | 0-2 |
| Northern Ireland Cup | 2021/05/08 16:30 | Glentoran v Cliftonville | L | 1-0 |
| Northern Ireland Premier | 2021/04/20 18:45 | Cliftonville v Glentoran | L | 0-2 |
| Northern Ireland Premier | 2021/02/06 15:00 | Glentoran v Cliftonville | L | 1-0 |
| Northern Ireland Premier | 2020/10/17 14:00 | Cliftonville v Glentoran | W | 1-0 |
| Northern Ireland Cup | 2020/07/27 19:00 | Cliftonville v Glentoran | L | 7-8 |
| Northern Ireland Premier | 2020/03/07 15:00 | Glentoran v Cliftonville | W | 0-2 |
| Northern Ireland Premier | 2019/11/30 15:00 | Cliftonville v Glentoran | L | 0-2 |
Home History
| Northern Ireland Premier | 2021/08/31 18:45 | Cliftonville v Coleraine | W | 2-1 |
| Northern Ireland Premier | 2021/08/28 14:00 | Cliftonville v Carrick Rangers | W | 2-1 |
| UK Friendlies | 2021/07/31 13:00 | Portstewart v Cliftonville | W | 1-3 |
| Club Friendly List | 2021/07/24 13:00 | Cliftonville v Newry City | W | 2-0 |
| Northern Ireland Play-Offs | 2021/06/05 16:30 | Larne FC v Cliftonville | L | 3-1 |
| Northern Ireland Premier | 2021/06/01 18:30 | Cliftonville v Crusaders | W | 5-4 |
| Northern Ireland Premier | 2021/05/29 16:30 | Cliftonville v Linfield | L | 0-2 |
| Northern Ireland Premier | 2021/05/25 18:45 | Cliftonville v Crusaders | D | 1-1 |
Away History
| Northern Ireland Premier | 2021/08/28 14:00 | Dungannon Swifts v Glentoran | W | 2-3 |
| UK Friendlies | 2021/08/21 14:00 | Glentoran v Crusaders | W | 3-1 |
| Club Friendly List | 2021/08/17 18:45 | Glentoran v Warrenpoint Town | W | 4-0 |
| Club Friendly List | 2021/08/03 18:30 | Dundela v Glentoran | W | 1-3 |
| UEFA Conference League Qualifying | 2021/07/15 17:15 | T.N.S. v Glentoran | L | 2-0 |
| UEFA Conference League Qualifying | 2021/07/08 17:45 | Glentoran v T.N.S. | D | 1-1 |
| UK Friendlies | 2021/07/02 18:00 | Glentoran v Dundela | W | 3-0 |
| Club Friendly List | 2021/06/26 13:00 | Glentoran v Coleraine | W | 1-0 |