Scottish League Cup 1999 |
| Round 1 | |||||||
|---|---|---|---|---|---|---|---|
| D 2 | Arbroath | 0 | 1 | Clydebank | D 1 | Gayfield Park | |
| D 2 | Brechin City | 2 | 2 | Hamilton Academical | D 1 | Glebe Park | aet 2-3p |
| D 2 | Clyde | 1 | 1 | Berwick Rangers | D 2 | Broadwood Stadium | aet 3-4p |
| D 2 | Cowdenbeath | 0 | 2 | Livingston | D 2 | Central Park | |
| D 2 | Dumbarton | 0 | 4 | Alloa Athletic | D 2 | Boghead Park | |
| D 2 | East Fife | 3 | 2 | Partick Thistle | D 2 | Bayview Stadium | |
| D 2 | Forfar Athletic | 0 | 1 | Stirling Albion | D 2 | Station Park | |
| D 2 | Queen of the South | 1 | 4 | Inverness Caledonian Thistle | D 2 | Palmerston Park | |
| D 2 | Queen's Park | 1 | 3 | Ayr United | D 1 | Hampden Park | |
| D 2 | Ross County | 4 | 1 | Montrose | D 2 | Victoria Park | |
| D 2 | Stenhousemuir | 1 | 0 | East Stirlingshire | D 2 | Ochilview Park | |
| D 1 | Stranraer | 1 | 1 | Albion Rovers | D 2 | Stair Park | aet 4-3p |
| Round 2 | |||||||
|---|---|---|---|---|---|---|---|
| D 2 | Berwick Rangers | 1 | 5 | Falkirk | D 1 | Shielfield Park | |
| SPL | Dundee | 0 | 1 | Alloa Athletic | D 2 | Dens Park | |
| SPL | Dundee United | 2 | 2 | Stirling Albion | D 2 | Tannadice Park | aet 3-0p |
| D 2 | East Fife | 0 | 1 | Motherwell | SPL | Bayview Stadium | aet |
| D 1 | Greenock Morton | 0 | 1 | Ross County | D 2 | Cappielow Park | |
| D 1 | Hamilton Academical | 1 | 2 | Hibernian | D 1 | Cliftonhill, Coatbridge | |
| D 2 | Inverness Caledonian Thistle | 0 | 3 | Aberdeen | SPL | Caledonian Stadium | |
| D 2 | Livingston | 1 | 0 | Dunfermline Athletic | SPL | Almondvale Stadium | aet |
| D 1 | Raith Rovers | 2 | 0 | Clydebank | D 1 | Stark's Park | |
| SPL | St Johnstone | 3 | 0 | Stranraer | D 1 | McDiarmid Park | |
| D 1 | St Mirren | 1 | 3 | Ayr United | D 1 | Love Street | |
| D 2 | Stenhousemuir | 0 | 2 | Airdrieonians | D 1 | Ochilview Park | |
| Round 3 | |||||||
|---|---|---|---|---|---|---|---|
| D 1 | Falkirk | 0 | 1 | St Johnstone | SPL | Brockville Park | |
| SPL | Kilmarnock | 3 | 1 | Livingston | D 2 | Rugby Park | aet |
| SPL | Motherwell | 0 | 2 | Ayr United | D 1 | Fir Park | |
| SPL | Rangers | 4 | 0 | Alloa Athletic | D 2 | Ibrox Stadium | |
| D 1 | Airdrieonians | 1 | 0 | Celtic | SPL | Excelsior Stadium | |
| SPL | Heart of Midlothian | 4 | 2 | Raith Rovers | D 1 | Tynecastle Park | aet |
| D 1 | Hibernian | 1 | 0 | Aberdeen | SPL | Easter Road | |
| D 2 | Ross County | 2 | 0 | Dundee United | SPL | Victoria Park | aet |
| Quarter Final | |||||||
|---|---|---|---|---|---|---|---|
| D 1 | Ayr United | 0 | 2 | Rangers | SPL | Somerset Park | |
| SPL | Kilmarnock | 0 | 1 | Airdrieonians | D 1 | Rugby Park | |
| SPL | St Johnstone | 4 | 0 | Hibernian | D 1 | McDiarmid Park | |
| SPL | Heart of Midlothian | 1 | 1 | Ross County | D 2 | Tynecastle Park | aet 3-0p |
| Semi Final | |||||||
|---|---|---|---|---|---|---|---|
| SPL | Rangers | 5 | 0 | Airdrieonians | D 1 | Easter Road, Edinburgh | |
| SPL | St Johnstone | 3 | 0 | Heart Of Midlothian | SPL | Parkhead, Glasgow | |
| Final | |||||||
|---|---|---|---|---|---|---|---|
| SPL | Rangers | 2 | 1 | St Johnstone | SPL | Parkhead, Glasgow | |