[3] Inverness CT 1-0 Raith [5] 2021-07-18 04:00
Stadium: Caledonian Stadium Round: 2
Referee: Alan James Muir Home Manager: John Robertson Away Manager: John McGlynn
Head to Head
| Scotland Championship | 2021/03/16 19:00 | Raith v Inverness CT | W | 0-1 |
| Scotland Championship | 2021/03/12 19:45 | Inverness CT v Raith | D | 0-0 |
| Scotland Championship | 2020/11/21 15:00 | Inverness CT v Raith | W | 2-0 |
| Scotland League Cup | 2020/11/10 19:45 | Raith v Inverness CT | L | 6-5 |
| Scotland League Cup | 2019/07/20 14:00 | Inverness CT v Raith | W | 4-1 |
| Scotland League Cup | 2018/07/24 18:45 | Inverness CT v Raith | W | 2-1 |
| Scotland FA Cup | 2015/03/10 19:45 | Inverness CT v Raith | W | 1-0 |
| Club Friendly List | 2014/07/19 14:00 | Raith v Inverness CT | W | 0-1 |
Home History
| Scotland League Cup | 2021/07/17 14:00 | Inverness CT v Stirling | L | 4-5 |
| Scotland League Cup | 2021/07/13 18:45 | Inverness CT v Peterhead | W | 2-0 |
| Europe Friendlies | 2021/06/23 18:30 | Clachnacuddin v Inverness CT | W | 0-5 |
| Scotland Championship | 2021/04/30 18:45 | Inverness CT v Ayr | D | 2-2 |
| Scotland Championship | 2021/04/24 14:00 | Hearts v Inverness CT | L | 3-0 |
| Scotland Championship | 2021/04/20 18:00 | Inverness CT v Dundee | D | 1-1 |
| Scotland FA Cup | 2021/04/16 17:00 | St Mirren v Inverness CT | L | 2-1 |
| Scotland Championship | 2021/04/10 14:00 | Queen of South v Inverness CT | D | 1-1 |
Away History
| UK Friendlies | 2021/07/16 18:00 | Raith v Hibernian | L | 1-3 |
| Scotland League Cup | 2021/07/13 18:45 | Raith v Brechin | W | 4-0 |
| Scotland League Cup | 2021/07/10 14:00 | Cowdenbeath v Raith | W | 0-1 |
| Club Friendly List | 2021/07/03 13:00 | Raith v Queen's Park | D | 2-2 |
| Club Friendly List | 2021/06/26 13:00 | Raith v Stranraer | W | 4-1 |
| Scotland Premiership Play-Offs | 2021/05/15 18:45 | Dundee v Raith | W | 0-1 |
| Scotland Premiership Play-Offs | 2021/05/12 18:45 | Raith v Dundee | L | 0-3 |
| Scotland Premiership Play-Offs | 2021/05/08 14:00 | Raith v Dunfermline | W | 2-0 |