| Final. Played at Hampden Park, Glasgow. | | date | time | Winner | score | Finalist | HT | att. | | Sun 15.03.09 | 15:00 | Celtic | 2-0 | Rangers | 0-0 | 0-0 | |
| date | time | Home | score | Away | HT | att. | | Tue 27.01.09 | 19:45 | Rangers | 3-0 | Falkirk | | | | Wed 28.01.09 | 19:45 | Celtic | 0-0 | Dundee United | 0-0 | 0-0 | 11-10 |
| date | time | Home | score | Away | HT | att. |
| date | time | Home | score | Away | HT | att. | | Tue 28.10.08 | 19:45 | Falkirk | 1-0 | Inverness CT | | | | Tue 28.10.08 | 19:45 | Rangers | 2-0 | Hamilton Academical | | | | Tue 28.10.08 | 19:45 | Dundee United | 1-0 | Dunfermline Athletic | | | | Wed 29.10.08 | 19:45 | Kilmarnock | 1-3 | Celtic | | |
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| date | time | Home | score | Away | HT | | | Tue 23.09.08 | 19:45 | Dundee United | 2-0 | Airdrie United | | | | Tue 23.09.08 | 19:45 | Greenock Morton | 1-2 | Inverness CT | | 0-0 | | | Tue 23.09.08 | 19:45 | Falkirk | 2-1 | Queen Of The South | | | | Tue 23.09.08 | 19:45 | Celtic | 4-0 | Livingston | | | | Tue 23.09.08 | 19:45 | Dunfermline Athletic | 2-0 | St. Mirren | | | | Wed 24.09.08 | 19:45 | Partick Thistle | 1-2 | Rangers | | 0-0 | | | Wed 24.09.08 | 19:45 | Motherwell | 1-2 | Hamilton Academical | | 0-0 | | | Wed 24.09.08 | 19:45 | Kilmarnock | 4-2 | Aberdeen | | |
| date | time | Home | score | Away | HT | att. | | Tue 26.08.08 | 19:45 | St. Mirren | 7-0 | Dumbarton | | | | Tue 26.08.08 | 19:45 | Livingston | 2-1 | St. Johnstone | | 0-0 | | | Tue 26.08.08 | 19:45 | Dundee | 1-2 | Partick Thistle | | | | Tue 26.08.08 | 19:45 | Hibernian | 3-4 | Greenock Morton | | 0-0 | | | Tue 26.08.08 | 19:45 | Hamilton Academical | 3-1 | Clyde | | | | Tue 26.08.08 | 19:45 | Cowdenbeath | 1-5 | Dundee United | | | | Tue 26.08.08 | 19:45 | Raith Rovers | 1-3 | Falkirk | | | | Tue 26.08.08 | 19:45 | Dunfermline Athletic | 1-0 | Alloa Athletic | | | | Wed 27.08.08 | 19:45 | Ayr United | 0-1 | Aberdeen | | | | Wed 27.08.08 | 19:45 | Arbroath | 0-0 | Inverness CT | 0-0 | 0-0 | 2-4 | | Wed 27.08.08 | 19:45 | Heart of Midlothian | 0-0 | Airdrie United | 0-0 | 0-0 | 3-4 | | Wed 27.08.08 | 19:45 | Brechin City | 0-2 | Kilmarnock | | |
| date | time | Home | score | Away | HT | att. | | Tue 05.08.08 | 19:30 | Dumbarton | 0-0 | Annan Athletic | 0-0 | 0-0 | 5-4 | | Tue 05.08.08 | 19:30 | Partick Thistle | 4-3 | Forfar Athletic | | 0-0 | | | Tue 05.08.08 | 19:30 | Stenhousemuir | 1-5 | St. Johnstone | | | | Tue 05.08.08 | 19:45 | Albion Rovers | 0-0 | Raith Rovers | 0-0 | 0-0 | 3-4 | | Tue 05.08.08 | 19:45 | Alloa Athletic | 2-0 | Elgin City | | | | Tue 05.08.08 | 19:45 | Clyde | 4-1 | Queen's Park | | | | Tue 05.08.08 | 19:45 | Montrose | 0-2 | Cowdenbeath | | | | Tue 05.08.08 | 19:45 | Peterhead | 0-2 | Dunfermline Athletic | | | | Tue 05.08.08 | 19:45 | Ross County | 2-3 | Airdrie United | | 0-0 | | | Tue 05.08.08 | 19:45 | Stranraer | 3-6 | Greenock Morton | | | | Wed 06.08.08 | 19:30 | East Stirlingshire | 1-2 | Livingston | | 0-0 | | | Wed 06.08.08 | 19:45 | Arbroath | 3-2 | Stirling Albion | | | | Wed 06.08.08 | 19:45 | East Fife | 0-3 | Brechin City | | | | Wed 06.08.08 | 19:45 | Ayr United | 2-1 | Berwick Rangers | | |
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Prepared and maintained by Todor Krastev
todor1966@yahoo.com
Last updated: 6 Jan 2019
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