1998-99 Scottish Cup
| Final | ||||||
| Rangers | 1 | 0 | Celtic | Sat 29 May 1999 | Details | |
| Semi Final | ||||||
| Celtic | 2 | 0 | Dundee United | Sat 10 Apr 1999 | Details | |
| St Johnstone | 0 | 4 | Rangers | Sun 11 Apr 1999 | Details | |
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| 5th Round | ||||||
| Motherwell | 0 | 2 | St Johnstone | Sat 06 Mar 1999 | Details | |
| Rangers | 2 | 1 | Falkirk | Sun 07 Mar 1999 | Details | |
| Greenock Morton | 0 | 3 | Celtic | Mon 08 Mar 1999 | Details | |
| Ayr United | 0 | 0 | Dundee United | Sat 13 Mar 1999 | Details | |
| Dundee United | 2 | 1 | Ayr United | Tue 16 Mar 1999 | 1st Replay | Details |
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| 4th Round | ||||||
| Ayr United | 1 | 0 | Albion Rovers | Sat 13 Feb 1999 | Details | |
| Livingston | 1 | 3 | St Johnstone | Sat 13 Feb 1999 | Details | |
| Stranraer | 1 | 2 | Falkirk | Sat 13 Feb 1999 | Details | |
| Greenock Morton | 6 | 1 | Clyde | Sat 13 Feb 1999 | Details | |
| Celtic | 4 | 0 | Dunfermline Athletic | Sat 13 Feb 1999 | Details | |
| Motherwell | 2 | 0 | Stirling Albion | Sat 13 Feb 1999 | Details | |
| Hamilton | 0 | 6 | Rangers | Sun 14 Feb 1999 | Details | |
| Clydebank | 2 | 2 | Dundee United | Wed 03 Mar 1999 | Details | |
| Dundee United | 3 | 0 | Clydebank | Sat 06 Mar 1999 | 1st Replay | Details |
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| 3rd Round | ||||||
| Ayr United | 3 | 0 | Kilmarnock | Sat 23 Jan 1999 | Details | |
| Hibernian | 1 | 1 | Stirling Albion | Sat 23 Jan 1999 | Details | |
| Raith Rovers | 0 | 4 | Clyde | Sat 23 Jan 1999 | Details | |
| Partick Thistle | 1 | 2 | Dunfermline Athletic | Sat 23 Jan 1999 | Details | |
| Brechin City | 1 | 1 | Albion Rovers | Sat 23 Jan 1999 | Details | |
| Rangers | 2 | 0 | Stenhousemuir | Sat 23 Jan 1999 | Details | |
| Aberdeen | 0 | 1 | Livingston | Sat 23 Jan 1999 | Details | |
| Celtic | 3 | 1 | Airdrieonians | Sat 23 Jan 1999 | Details | |
| Falkirk | 3 | 0 | Huntly | Sat 23 Jan 1999 | Details | |
| St Johnstone | 1 | 0 | Forfar Athletic | Sat 23 Jan 1999 | Details | |
| St Mirren | 1 | 1 | Hamilton | Sat 23 Jan 1999 | Details | |
| Stranraer | 1 | 0 | East Stirlingshire | Sat 23 Jan 1999 | Details | |
| Greenock Morton | 2 | 1 | Dundee | Sat 23 Jan 1999 | Details | |
| Motherwell | 3 | 1 | Hearts | Sun 24 Jan 1999 | Details | |
| Stirling Albion | 2 | 1 | Hibernian | Tue 02 Feb 1999 | 1st Replay | Details |
| Albion Rovers | 3 | 1 | Brechin City | Tue 02 Feb 1999 | 1st Replay | Details |
| Queen's Park | 0 | 0 | Dundee United | Tue 02 Feb 1999 | Details | |
| Hamilton | 1 | 0 | St Mirren | Tue 02 Feb 1999 | 1st Replay | Details |
| Clydebank | 1 | 1 | Ross County | Wed 03 Feb 1999 | Details | |
| Dundee United | 1 | 0 | Queen's Park | Tue 09 Feb 1999 | 1st Replay | Details |
| Ross County | 2 | 3 | Clydebank | Mon 15 Feb 1999 | 1st Replay | Details |
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| 2nd Round | ||||||
| Montrose | 0 | 0 | Stirling Albion | Sat 02 Jan 1999 | Details | |
| Civil Service Strollers | 0 | 3 | Albion Rovers | Sat 02 Jan 1999 | Details | |
| Keith | 0 | 0 | Brechin City | Sat 02 Jan 1999 | Details | |
| Spartans | 1 | 1 | Clyde | Sat 02 Jan 1999 | Details | |
| Huntly | 3 | 0 | Peterhead | Sat 02 Jan 1999 | Details | |
| Inverness Caledonian Thistle | 1 | 2 | Livingston | Sat 02 Jan 1999 | Details | |
| Whitehill | 1 | 1 | Stenhousemuir | Sat 02 Jan 1999 | Details | |
| Forfar Athletic | 2 | 2 | East Fife | Sat 02 Jan 1999 | Details | |
| Dalbeattie Star | 1 | 2 | East Stirlingshire | Sat 02 Jan 1999 | Details | |
| Partick Thistle | 5 | 2 | Cowdenbeath | Sat 02 Jan 1999 | Details | |
| Clyde | 5 | 0 | Spartans | Wed 06 Jan 1999 | 1st Replay | Details |
| Brechin City | 3 | 1 | Keith | Sat 09 Jan 1999 | 1st Replay | Details |
| Stenhousemuir | 2 | 0 | Whitehill | Sat 09 Jan 1999 | 1st Replay | Details |
| East Fife | 0 | 1 | Forfar Athletic | Sat 09 Jan 1999 | 1st Replay | Details |
| Queen Of The South | 1 | 3 | Ross County | Sat 09 Jan 1999 | Details | |
| Queen's Park | 1 | 1 | Clachnacuddin | Mon 18 Jan 1999 | Details | |
| Stirling Albion | 2 | 1 | Montrose | Mon 18 Jan 1999 | 1st Replay | Details |
| Clachnacuddin | 2 | 3 | Queen's Park | Sat 23 Jan 1999 | 1st Replay | Details |
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| 1st Round | ||||||
| Stenhousemuir | 1 | 1 | Alloa Athletic | Sat 05 Dec 1998 | Details | |
| Arbroath | 1 | 2 | Partick Thistle | Sat 05 Dec 1998 | Details | |
| Dumbarton | 1 | 1 | Livingston | Sat 05 Dec 1998 | Details | |
| Queen's Park | 2 | 0 | Berwick Rangers | Sat 05 Dec 1998 | Details | |
| Livingston | 3 | 0 | Dumbarton | Tue 08 Dec 1998 | 1st Replay | Details |
| Alloa Athletic | 0 | 2 | Stenhousemuir | Sat 12 Dec 1998 | 1st Replay | Details |
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