Scottish League Cup competition results from 1999/2000
A full listing of matches played in the competition throughout the season
| Final | ||||
|---|---|---|---|---|
| Sunday, 19th March 2000 | ||||
| Celtic (SPL) | 2 | Aberdeen (SPL) | 0 | |
| played at Hampden Park | ||||
| Semi Final | ||||
|---|---|---|---|---|
| Sunday, 13th February 2000 | ||||
| Aberdeen (SPL) | 1 | Dundee United (SPL) | 0 | |
| played at Dens Park | ||||
| Wednesday, 16th February 2000 | ||||
| Celtic (SPL) | 1 | Kilmarnock (SPL) | 0 | |
| played at Hampden Park | ||||
| Quarter Final | ||||
|---|---|---|---|---|
| Wednesday, 1st December 1999 | ||||
| Aberdeen (SPL) | 1 | Rangers (SPL) | 0 | |
| Celtic (SPL) | 1 | Dundee (SPL) | 0 | |
| Dundee United (SPL) | 3 | Motherwell (SPL) | 2 | |
| Wednesday, 2nd February 2000 | ||||
| Kilmarnock (SPL) | 1 | Heart of Midlothian (SPL) | 0 | |
| 3rd Round | ||||
|---|---|---|---|---|
| Tuesday, 12th October 1999 | ||||
| Aberdeen (SPL) | 1 | Falkirk (SCD1) | 1 | |
| Aberdeen won 5-3 on penalties | ||||
| Alloa Athletic (SCD2) | 1 | Dundee (SPL) | 3 | |
| East Fife (SCD3) | 0 | Heart of Midlothian (SPL) | 2 | |
| Inverness Caledonian Thistle (SCD1) | 0 | Motherwell (SPL) | 1 | |
| Kilmarnock (SPL) | 3 | Hibernian (SPL) | 2 | |
| Rangers (SPL) | 1 | Dunfermline Athletic (SCD1) | 0 | |
| St. Johnstone (SPL) | 1 | Dundee United (SPL) | 2 | |
| Wednesday, 13th October 1999 | ||||
| Ayr United (SCD1) | 0 | Celtic (SPL) | 4 | |
| 2nd Round | ||||
|---|---|---|---|---|
| Tuesday, 17th August 1999 | ||||
| Aberdeen (SPL) | 1 | Livingston (SCD1) | 0 | |
| Ayr United (SCD1) | 2 | Hamilton Academical (SCD2) | 1 | |
| Clyde (SCD2) | 2 | Hibernian (SPL) | 2 | |
| Hibernian won 5-4 on penalties | ||||
| Dundee (SPL) | 4 | Dumbarton (SCD3) | 0 | |
| East Fife (SCD3) | 2 | Airdrieonians (SCD1) | 2 | |
| East Fife won 5-4 on penalties | ||||
| Greenock Morton (SCD1) | 1 | Alloa Athletic (SCD2) | 3 | |
| Inverness Caledonian Thistle (SCD1) | 2 | St. Mirren (SCD1) | 0 | |
| Wednesday, 18th August 1999 | ||||
| Dundee United (SPL) | 3 | Ross County (SCD2) | 1 | |
| Dunfermline Athletic (SCD1) | 4 | Queen's Park (SCD3) | 0 | |
| East Stirlingshire (SCD3) | 0 | Falkirk (SCD1) | 2 | |
| Queen of the South (SCD2) | 1 | Heart of Midlothian (SPL) | 3 | |
| Raith Rovers (SCD1) | 2 | Motherwell (SPL) | 2 | |
| Motherwell won 5-4 on penalties | ||||
| 1st Round | ||||
|---|---|---|---|---|
| Saturday, 31st July 1999 | ||||
| Albion Rovers (SCD3) | 0 | Clyde (SCD2) | 3 | |
| Brechin City (SCD3) | 0 | Dumbarton (SCD3) | 2 | |
| Clydebank (SCD1) | 1 | East Stirlingshire (SCD3) | 2 | |
| Cowdenbeath (SCD3) | 0 | Livingston (SCD1) | 2 | |
| East Fife (SCD3) | 2 | Stirling Albion (SCD2) | 2 | |
| East Fife won 8-7 on penalties | ||||
| Montrose (SCD3) | 1 | Hamilton Academical (SCD2) | 2 | |
| Partick Thistle (SCD2) | 0 | Alloa Athletic (SCD2) | 2 | |
| Queen of the South (SCD2) | 1 | Arbroath (SCD2) | 0 | |
| Queen's Park (SCD3) | 2 | Berwick Rangers (SCD3) | 1 | |
| Ross County (SCD2) | 2 | Forfar Athletic (SCD3) | 1 | |
| Stenhousemuir (SCD2) | 1 | Inverness Caledonian Thistle (SCD1) | 3 | |
| Stranraer (SCD2) | 0 | Raith Rovers (SCD1) | 1 | |
