Scottish League Cup competition results from 2008/2009
A full listing of matches played in the competition throughout the season
| 3rd Round |
| Tuesday, 23rd September 2008 |
| Celtic (SPL) | 4 | Livingston (SCD1) | 0 | 23,569 |
| Dundee United (SPL) | 2 | Airdrie United (SCD1) | 0 | 3,444 |
| Dunfermline Athletic (SCD1) | 2 | St. Mirren (SPL) | 0 | 2,186 |
| Falkirk (SPL) | 2 | Queen of the South (SCD1) | 1 | 2,058 |
| Greenock Morton (SCD1) | 1 | Inverness Caledonian Thistle (SPL) | 2 | 2,023 |
| Wednesday, 24th September 2008 |
| Kilmarnock (SPL) | 4 | Aberdeen (SPL) | 2 | 4,339 |
| Motherwell (SPL) | 1 | Hamilton Academical (SPL) | 2 | 5,590 |
| after extra time, 90 minutes 1-1 |
| Partick Thistle (SCD1) | 1 | Rangers (SPL) | 2 | 6,497 |
| after extra time, 90 minutes 1-1 |
| 2nd Round |
| Tuesday, 26th August 2008 |
| Cowdenbeath (SCD3) | 1 | Dundee United (SPL) | 5 | 1,438 |
| Dundee (SCD1) | 1 | Partick Thistle (SCD1) | 2 | 2,507 |
| Dunfermline Athletic (SCD1) | 1 | Alloa Athletic (SCD2) | 0 | 1,326 |
| Hamilton Academical (SPL) | 3 | Clyde (SCD1) | 1 | 1,146 |
| Hibernian (SPL) | 3 | Greenock Morton (SCD1) | 4 | 14,874 |
| after extra time, 90 minutes 2-2 |
| Livingston (SCD1) | 2 | St. Johnstone (SCD1) | 1 | 979 |
| after extra time, 90 minutes 1-1 |
| Raith Rovers (SCD2) | 1 | Falkirk (SPL) | 3 | 2,040 |
| St. Mirren (SPL) | 7 | Dumbarton (SCD3) | 0 | 1,747 |
| Wednesday, 27th August 2008 |
| Arbroath (SCD2) | 2 | Inverness Caledonian Thistle (SPL) | 2 | 596 |
| after extra time, 90 minutes 2-2, Inverness Caledonian Thistle won 4-2 on penalties |
| Ayr United (SCD2) | 0 | Aberdeen (SPL) | 1 | 2,979 |
| Brechin City (SCD2) | 0 | Kilmarnock (SPL) | 2 | 802 |
| Heart of Midlothian (SPL) | 0 | Airdrie United (SCD1) | 0 | 6,844 |
| after extra time, Airdrie United won 4-3 on penalties |
| 1st Round |
| Tuesday, 5th August 2008 |
| Albion Rovers (SCD3) | 0 | Raith Rovers (SCD2) | 0 | 415 |
| after extra time, 90 minutes 0-0, Raith Rovers won 4-3 on penalties |
| Alloa Athletic (SCD2) | 2 | Elgin City (SCD3) | 0 | 269 |
| Clyde (SCD1) | 4 | Queen's Park (SCD2) | 1 | 690 |
| Dumbarton (SCD3) | 1 | Annan Athletic (SCD3) | 1 | 462 |
| after extra time, 90 minutes 0-0, Dumbarton won 5-4 on penalties |
| Montrose (SCD3) | 0 | Cowdenbeath (SCD3) | 2 | 382 |
| Partick Thistle (SCD1) | 4 | Forfar Athletic (SCD3) | 3 | 1,192 |
| after extra time, 90 minutes 2-2 |
| Peterhead (SCD2) | 0 | Dunfermline Athletic (SCD1) | 2 | 1,291 |
| Ross County (SCD1) | 2 | Airdrie United (SCD1) | 3 | 869 |
| after extra time, 90 minutes 2-2 |
| Stenhousemuir (SCD3) | 1 | St. Johnstone (SCD1) | 5 | 687 |
| Stranraer (SCD2) | 3 | Greenock Morton (SCD1) | 6 | 317 |
| Wednesday, 6th August 2008 |
| Arbroath (SCD2) | 3 | Stirling Albion (SCD2) | 2 | 448 |
| Ayr United (SCD2) | 2 | Berwick Rangers (SCD3) | 1 | 745 |
| East Fife (SCD2) | 0 | Brechin City (SCD2) | 3 | 523 |
| East Stirlingshire (SCD3) | 1 | Livingston (SCD1) | 2 | 360 |
| after extra time, 90 minutes 1-1 |
