1958-59 Scottish Cup
| Final | ||||||
| St Mirren | 3 | 1 | Aberdeen | Sat 25 Apr 1959 | Details | |
| Semi Final | ||||||
| St Mirren | 4 | 0 | Celtic | Sat 04 Apr 1959 | Details | |
| Aberdeen | 1 | 1 | Third Lanark | Sat 04 Apr 1959 | Details | |
| Aberdeen | 1 | 0 | Third Lanark | Wed 08 Apr 1959 | 1st Replay | Details |
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| 4th Round | ||||||
| Aberdeen | 3 | 1 | Kilmarnock | Sat 14 Mar 1959 | Details | |
| Third Lanark | 2 | 1 | Hibernian | Sat 14 Mar 1959 | Details | |
| St Mirren | 2 | 1 | Dunfermline Athletic | Sat 14 Mar 1959 | Details | |
| Stirling Albion | 1 | 3 | Celtic | Sat 14 Mar 1959 | Details | |
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| 3rd Round | ||||||
| Hibernian | 4 | 1 | Partick Thistle | Sat 28 Feb 1959 | Details | |
| St Mirren | 3 | 2 | Motherwell | Sat 28 Feb 1959 | Details | |
| Hamilton | 0 | 5 | Kilmarnock | Sat 28 Feb 1959 | Details | |
| Celtic | 2 | 1 | Rangers | Sat 28 Feb 1959 | Details | |
| Dunfermline Athletic | 2 | 1 | Ayr United | Sat 28 Feb 1959 | Details | |
| Stirling Albion | 3 | 1 | Greenock Morton | Sat 28 Feb 1959 | Details | |
| Third Lanark | 3 | 2 | Alloa Athletic | Sat 28 Feb 1959 | Details | |
| St Johnstone | 1 | 2 | Aberdeen | Sat 28 Feb 1959 | Details | |
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| 2nd Round | ||||||
| St Mirren | 10 | 0 | Peebles Rovers | Fri 13 Feb 1959 | Details | |
| Dundee United | 0 | 4 | Third Lanark | Sat 14 Feb 1959 | Details | |
| Brechin City | 3 | 3 | Alloa Athletic | Sat 14 Feb 1959 | Details | |
| Babcock and Wilcox | 0 | 5 | Greenock Morton | Sat 14 Feb 1959 | Details | |
| Coldstream | 0 | 4 | Hamilton | Sat 14 Feb 1959 | Details | |
| Montrose | 0 | 1 | Dunfermline Athletic | Sat 14 Feb 1959 | Details | |
| Stenhousemuir | 1 | 3 | Partick Thistle | Sat 14 Feb 1959 | Details | |
| Airdrieonians | 2 | 7 | Motherwell | Sat 14 Feb 1959 | Details | |
| Dumbarton | 2 | 8 | Kilmarnock | Sat 14 Feb 1959 | Details | |
| Ayr United | 3 | 0 | Stranraer | Sat 14 Feb 1959 | Details | |
| St Johnstone | 3 | 1 | Queen's Park | Sat 14 Feb 1959 | Details | |
| Fraserburgh | 3 | 4 | Stirling Albion | Sat 14 Feb 1959 | Details | |
| Hibernian | 3 | 1 | Falkirk | Sat 14 Feb 1959 | Details | |
| Rangers | 3 | 2 | Hearts | Sat 14 Feb 1959 | Details | |
| Aberdeen | 3 | 0 | Arbroath | Sat 14 Feb 1959 | Details | |
| Alloa Athletic | 3 | 1 | Brechin City | Wed 18 Feb 1959 | 1st Replay | Details |
| Celtic | 1 | 1 | Clyde | Wed 18 Feb 1959 | Details | |
| Clyde | 3 | 4 | Celtic | Mon 23 Feb 1959 | 1st Replay | Details |
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| 1st Round | ||||||
| Dumbarton | 4 | 0 | Buckie Thistle | Sat 31 Jan 1959 | Details | |
| Stenhousemuir | 5 | 2 | Eyemouth United | Sat 31 Jan 1959 | Details | |
| Fraserburgh | 1 | 0 | Dundee | Sat 31 Jan 1959 | Details | |
| Aberdeen | 2 | 1 | East Fife | Sat 31 Jan 1959 | Details | |
| Peebles Rovers | 2 | 0 | Ross County | Sat 31 Jan 1959 | Details | |
| Queen Of The South | 1 | 3 | Hearts | Sat 31 Jan 1959 | Details | |
| East Stirlingshire | 1 | 1 | Dundee United | Sat 31 Jan 1959 | Details | |
| Celtic | 4 | 0 | Albion Rovers | Sat 31 Jan 1959 | Details | |
| Raith Rovers | 1 | 1 | Hibernian | Sat 31 Jan 1959 | Details | |
| Babcock and Wilcox | 4 | 0 | Forres Mechanics | Sat 31 Jan 1959 | Details | |
| Forfar Athletic | 1 | 3 | Rangers | Sat 31 Jan 1959 | Details | |
| Cowdenbeath | 2 | 2 | Dunfermline Athletic | Sat 31 Jan 1959 | Details | |
| Stranraer | 3 | 2 | Berwick Rangers | Sat 31 Jan 1959 | Details | |
| Dunfermline Athletic | 4 | 1 | Cowdenbeath | Mon 09 Feb 1959 | 1st Replay | Details |
| Hibernian | 2 | 1 | Raith Rovers | Mon 09 Feb 1959 | 1st Replay | Details |
| Dundee United | 0 | 0 | East Stirlingshire | Tue 10 Feb 1959 | 1st Replay | Details |
| Dundee United | 4 | 0 | East Stirlingshire | Wed 11 Feb 1959 | 2nd Replay | Details |
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