1999-00 Scottish Cup
| Final | ||||||
| Aberdeen | 0 | 4 | Rangers | Sat 27 May 2000 | Details | |
| Semi Final | ||||||
| Ayr United | 0 | 7 | Rangers | Sat 08 Apr 2000 | Details | |
| Hibernian | 1 | 2 | Aberdeen | Sun 09 Apr 2000 | Details | |
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| 5th Round | ||||||
| Ayr United | 2 | 0 | Partick Thistle | Sat 11 Mar 2000 | Details | |
| Hibernian | 3 | 1 | Falkirk | Sat 11 Mar 2000 | Details | |
| Dundee United | 0 | 1 | Aberdeen | Sun 12 Mar 2000 | Details | |
| Rangers | 4 | 1 | Hearts | Sun 12 Mar 2000 | Details | |
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| 4th Round | ||||||
| Partick Thistle | 2 | 1 | Livingston | Sat 19 Feb 2000 | Details | |
| Greenock Morton | 0 | 1 | Rangers | Sat 19 Feb 2000 | Details | |
| Alloa Athletic | 2 | 2 | Dundee United | Sat 19 Feb 2000 | Details | |
| Hibernian | 1 | 1 | Clydebank | Sat 19 Feb 2000 | Details | |
| Berwick Rangers | 0 | 0 | Falkirk | Sat 19 Feb 2000 | Details | |
| Clyde | 0 | 2 | Hearts | Sat 19 Feb 2000 | Details | |
| Inverness Caledonian Thistle | 1 | 1 | Aberdeen | Sun 20 Feb 2000 | Details | |
| Dundee United | 4 | 0 | Alloa Athletic | Tue 22 Feb 2000 | 1st Replay | Details |
| Motherwell | 3 | 4 | Ayr United | Sat 26 Feb 2000 | Details | |
| Aberdeen | 1 | 0 | Inverness Caledonian Thistle | Tue 29 Feb 2000 | 1st Replay | Details |
| Clydebank | 0 | 3 | Hibernian | Tue 29 Feb 2000 | 1st Replay | Details |
| Falkirk | 3 | 0 | Berwick Rangers | Tue 29 Feb 2000 | 1st Replay | Details |
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| 3rd Round | ||||||
| Stranraer | 1 | 2 | Berwick Rangers | Sat 29 Jan 2000 | Details | |
| Queen Of The South | 0 | 7 | Livingston | Sat 29 Jan 2000 | Details | |
| Clydebank | 1 | 0 | Stirling Albion | Sat 29 Jan 2000 | Details | |
| St Mirren | 1 | 1 | Aberdeen | Sat 29 Jan 2000 | Details | |
| Clyde | 3 | 1 | Raith Rovers | Sat 29 Jan 2000 | Details | |
| Falkirk | 3 | 1 | Peterhead | Sat 29 Jan 2000 | Details | |
| Hearts | 3 | 2 | Stenhousemuir | Sat 29 Jan 2000 | Details | |
| Albion Rovers | 1 | 2 | Partick Thistle | Sat 29 Jan 2000 | Details | |
| Dundee | 0 | 0 | Ayr United | Sat 29 Jan 2000 | Details | |
| Hibernian | 4 | 1 | Dunfermline Athletic | Sat 29 Jan 2000 | Details | |
| St Johnstone | 0 | 2 | Rangers | Sun 30 Jan 2000 | Details | |
| Dundee United | 4 | 1 | Airdrieonians | Sun 30 Jan 2000 | Details | |
| Greenock Morton | 1 | 1 | Brechin City | Sun 30 Jan 2000 | Details | |
| Arbroath | 1 | 1 | Motherwell | Tue 01 Feb 2000 | Details | |
| Kilmarnock | 0 | 0 | Alloa Athletic | Sat 05 Feb 2000 | Details | |
| Celtic | 1 | 3 | Inverness Caledonian Thistle | Tue 08 Feb 2000 | Details | |
| Brechin City | 0 | 0 | Greenock Morton | Tue 08 Feb 2000 | 1st Replay | Details |
| Aberdeen | 2 | 0 | St Mirren | Tue 08 Feb 2000 | 1st Replay | Details |
| Alloa Athletic | 1 | 0 | Kilmarnock | Wed 09 Feb 2000 | 1st Replay | Details |
| Ayr United | 1 | 1 | Dundee | Tue 15 Feb 2000 | 1st Replay | Details |
| Motherwell | 2 | 0 | Arbroath | Sat 19 Feb 2000 | 1st Replay | Details |
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| 2nd Round | ||||||
| Brechin City | 2 | 2 | Annan Athletic | Sat 08 Jan 2000 | Details | |
| Montrose | 1 | 3 | Queen Of The South | Sat 08 Jan 2000 | Details | |
| Albion Rovers | 0 | 0 | Dalbeattie Star | Sat 08 Jan 2000 | Details | |
| Queen's Park | 1 | 2 | Berwick Rangers | Sat 08 Jan 2000 | Details | |
| Peterhead | 2 | 1 | Forfar Athletic | Sat 08 Jan 2000 | Details | |
| Cowdenbeath | 2 | 3 | Clyde | Sat 08 Jan 2000 | Details | |
| Stirling Albion | 2 | 1 | East Fife | Sat 08 Jan 2000 | Details | |
| Whitehill | 2 | 2 | Alloa Athletic | Sat 08 Jan 2000 | Details | |
| Arbroath | 0 | 0 | Fraserburgh | Sat 08 Jan 2000 | Details | |
| Stranraer | 1 | 0 | Clachnacuddin | Sat 08 Jan 2000 | Details | |
| Partick Thistle | 2 | 1 | East Stirlingshire | Sat 08 Jan 2000 | Details | |
| Dumbarton | 0 | 2 | Stenhousemuir | Sat 08 Jan 2000 | Details | |
| Annan Athletic | 2 | 3 | Brechin City | Sat 15 Jan 2000 | 1st Replay | Details |
| Fraserburgh | 1 | 3 | Arbroath | Sat 15 Jan 2000 | 1st Replay | Details |
| Dalbeattie Star | 1 | 5 | Albion Rovers | Wed 19 Jan 2000 | 1st Replay | Details |
| Alloa Athletic | 2 | 0 | Whitehill | Sat 29 Jan 2000 | 1st Replay | Details |
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| 1st Round | ||||||
| Hamilton | 1 | 2 | Clyde | Sat 11 Dec 1999 | Details | |
| Huntly | 0 | 1 | East Stirlingshire | Sat 11 Dec 1999 | Details | |
| Ross County | 2 | 2 | Forfar Athletic | Sat 11 Dec 1999 | Details | |
| Threave Rovers | 1 | 7 | Stenhousemuir | Mon 27 Dec 1999 | Details | |
| Forfar Athletic | 0 | 0 | Ross County | Mon 03 Jan 2000 | 1st Replay | Details |
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